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There's an interesting similar case in the WAFL. In 1978, East Perth and Perth met in the WAFL Grand Final. This wasn't unusual at the time, East Perth and Perth had played in the 1966, 1967, 1968 and 1976 Grand Finals, the Perth Demons winning all of these, but the East Perth Royals won a thriller over Perth in teeming rain in 1978.

East Perth would have been confident of winning some more premierships in coming years, while Perth having won the WAFL in 1976 and 1977 would have been aiming to make it three flags in four years by taking out the 1979 WAFL Premiership.

However, it would take 18 long years before either of these teams would make a Grand Final again, East Perth losing the 1996 decider to Claremont, before the Royals would break their 22-year premiership drought in 2000 and would win the 2001 and 2002 flags too. Perth have not made a Grand Final in 45 years since then, have finished at or near the bottom of the ladder on many occasions, and their finals appearances have been few and far between, in 1986, 1991, 1997 and the COVID affected 2020 season.

I couldn't find any instances of this in the SANFL or VFL/VFA - in most Grand Finals where a less successful team has made it there has always been a powerhouse like Port Adelaide, Norwood or Glenelg in SA; or a Port Melbourne, Williamstown or Sandringham in Victoria.

In the Talent League the Northern Knights played the NSW-ACT Rams in the 1996 Grand Final. The Knights were going for - and won - their fourth premiership in a row, while the Rams did well to make the GF from 7th spot in their first season and were far from disgraced. Twenty seven years later, the Northern Knights have not made another Grand Final, while the Rams mainly struggled throughout the rest of their tenure as a full-time Under 18's team in the late 1990s and early 2000s, before they withdrew from full-time competition at the end of 2002 and from there on played 4 games a season on an invitational basis.
In the NWFL in Tasmania in 2021 Devonport played Penguin for the premiership.
At the time Devonport hadn't won a flag for 33 years since winning the 1988 TFL Statewide League premiership and Penguin had gone 36 years without a flag, having previously won the 1985 NWFU premiership over Smithton in the days where the old three regional competitions were still operating prior to the TFL going statewide.

Currently in the Southern Football League in Tasmania, there are three clubs with long premiership droughts, Sorell last won a flag in 1990, Brighton's last one was 1998 and former TFL club Hobart hasn't won one since 1999.
 
Longest premiership droughts of currently existing Tasmanian football clubs that will be participating in the 2024 season.

60 years – Campania (Oatlands District FA)
Last title: 1963 South Eastern Districts FA.

38 years – West Ulverstone (NWFA)
Last title: 1985 Darwin FA.

38 years – Penguin (NWFL)
Last title: 1985 NWFU.

35 years – East Devonport (NWFL)
Last title: 1988 NTFL.

33 years – Sorell (Southern FL)
Last title: 1990 TAFL Southern Division.

33 years – Perth (NTFA Division One)
Last title: 1990 Esk-Deloraine FA.

32 years – Lauderdale (TSL)
Last title: 1991 TAFL Southern Division.

32 years – Smithton/Circular Head (NWFL)
Last title: 1991 NTFL.

30 years – Evandale (NTFA Division One)
Last title: 1993 Esk-Deloraine FA.

25 years – Mangalore/Brighton (Southern FL)
Last title: 1998 Southern FL.

25 years – Yeoman (Darwin FA)
Last title: 1998 Darwin FA.

24 years – Hobart (Southern FL)
Last title: 1999 Southern FL.

24 years – Rosebery-Toorak (NWFA)
Last title: 1999 NWFA.

23 years – Cuprona (Darwin FA)
Last title: 2000 Darwin FA.

22 years – Scottsdale (NTFA Premier Division)
Last title: 2001 NTFA Division One/Premier.

22 years – Campbell Town (Oatlands District FA)
Last title: 2001 NTFA Division Two/One.

21 years – East Ulverstone (NWFA)
Last title: 2002 NWFA.

20 years – North Hobart (TSL)
Last title: 2003 SFL Premier League.

20 years – Sheffield (NWFA)
Last title: 2003 NWFA.
 

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I became curious to see whether I could discover which player had made the most bounces during a passage of play, which occurs usually when a player goes on a long run and then has a shot on goal. Via YouTube I found three instances of players having seven bounces. The most bounces I discovered were:

7 Michael Mitchell, Richmond vs Sydney, round 22, 1990, SCG (kicked a goal)
7 Mick McGuane, Collingwood vs Carlton, round 2, 1994, MCG (goal)
7 Brent Harvey, North Melbourne vs West Coast, round 3, 2010, Docklands (behind: hit the post)
5 Daniel Kerr, West Coast vs Fremantle, round 22, 2003, Subiaco (goal)
5 Stephen Hill, Fremantle vs Geelong, 2nd qualifying final 2013, Kardinia Park (goal)

One thing I noticed was that many famous long-running goals occurred during the fourth quarter. Of the above all except McGuane (second quarter) occurred during the fourth. Other long-running goals I looked at were:

4 bounces Ray Gabelich, Collingwood vs Melbourne, grand final, 1964, MCG (4th quarter)
4 bounces Phil Manassa, Collingwood vs North Melbourne, grand final replay, 1977, MCG (4th quarter)
4 bounces Michael Long, Essendon vs Carlton, grand final, 1993, MCG (1st quarter)
3 bounces David Twomey, Collingwood vs North Melbourne, round 9, 1981, Arden Street (3rd quarter)
3 bounces Lance Franklin, Hawthorn vs Essendon, round 13, 2010, MCG (4th quarter)
3 bounces Lewis Jetta, Sydney vs Collingwood, 2nd preliminary final, 2012, Stadium Australia (1st quarter)
3 bounces Matt White, Port Adelaide vs Richmond, round 17, 2014, Docklands (4th quarter)

I have discovered this 9-bounce effort by Leigh Montagna on YouTube. It begins when he marks the ball at the 10:55 mark of the video.

 
Examples of teams who went from wooden spoon to premiers in the space of two years (from footy.fandom.com):

Wooden spoon to premiers:
Barossa District (Barossa Light & Gawler FL) - 2015-2016 (between 2012-2017: 2 flags, 2 spoons, 2 flags)
Benambra (Omeo District FL) - 1999-2000
Cudgewa (Upper Murray FL) - 1998-1999
Cunderdin (Avon FA) - 2019-2021 (COVID 2020, before COVID a threepeat of spoons, after COVID a threepeat of flags)
Dampier (North Pilbara FL) - 2020-2021 (threepeat after)
Denmark (Great Southern FL) - 2009-2010
Dudley United (Kangaroo Island FL) - 2013-2014 (threepeat after)
East Carnarvon (Gascoyne FA) - 2002-2003
Gibson (Esperance DFL) - 2008-2009
Imperials (Lower South West FL) - 2006-2007
Imperials (Sunraysia FL) - 2012-2013
Jamestown/Peterborough (Northern Areas FA) - 2013-2014
Jurien Bay (Central Midlands Coastal FA) - 2022-2023
Kalannie (Central Wheatbelt FL) - 2021-2022
Kingscote (Kangaroo Island FL) - 2017-2018
Lyrup (Riverland Independent FL) - 2003-2004, 2009-2010
Mullewa (Great Northern FL) - 2016-2017
Newtown/Condingup (Esperance DFL) - 2009-2010 (five spoons after), 2021-2022
North Whyalla (Whyalla FL) - 2007-2008
Orbost (East Gippsland FL) - 1997-1998
Port Wakefield (Adelaide Plains FL) - 1991-1992
Portarlington (Bellarine FL) - 1991-1992
Ramblers (Gascoyne FA) - 1996-1997 (unconfirmed position in 1996)
Rennie (Picola & District FL South East) - 2016-2017
Tallangatta (Tallangata & District FL) - 2014-2015
Tigers (Lower South West FL) - 2012-2013
Wanderers (Upper Great Southern FL) - 2020-2021
Warriors (Gascoyne FA) - 2018-2019
West Augusta (Spencer Gulf FL) - 1995-1996, 2012-2013
West Whyalla (Whyalla FL) - 2004-2005
Western Districts (Kangaroo Island FL) - 2016-2017
Wickepin (Upper Great Southern FL) - 2006-2007
Wongan Hills/Ballidu (Mortlock FL) - 2015-2016

Premiers to wooden spoon:
Bambill (Millewa FL) - 2016-2017 (coming off a threepeat)
Barossa District (Barossa Light & Gawler FL) - 2013-2014
Benambra (Omeo District FL) - 1994-1995, 2000-2001
Calingiri (Mortlock FL) - 2015-2016
Cobdogla (Riverland Independent FL) - 2001-2002
Cudgewa (Upper Murray FL) - 2000-2001
Donald (North Central FL) - 2006-2007
Esperance (Esperance DFL) - 2001-2002
Federals (Upper Murray FL) - 2007-2008
Hamley Bridge (Adelaide Plains FL) - 2014-2015
Jamestown/Peterborough (Northern Areas FA) - 2004-2005 (four spoons in a row after back-to-back premierships)
Loxton North (Riverland FL A Grade) - 2004-2005
Millicent (Western Border FL) - 2018-2019
Mullewa (Great Northern FL) - 2017-2018 (four spoons in a row)
Newcomb (Bellarine FL) - 2007-2008 (did not finish above second last until 2019)
Newtown/Condingup (Esperance DFL) - 2022-2023
Orbost (East Gippsland FL) - 1996-1997
Portarlington (Bellarine FL) - 1994-1995
Ports (Esperance DFL) - 2019-2020
Renmark (Riverland FL A Grade) - 2009-2010
Southern Flinders (Northern Areas FA) - 2013-2014
Wisanger (Kangaroo Island FL) - 2005-2006 (four spoons in a row)

The Northern Areas FA 2013-2014 and Mortlock FL 2015-2016 seasons are the only ones I've found in recent times where the premiers and wooden spooners switched places.
 
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Examples of teams who went from wooden spoon to premiers in the space of two years (from footy.fandom.com):

Wooden spoon to premiers:
Barossa District (Barossa Light & Gawler FL) - 2015-2016 (between 2012-2017: 2 flags, 2 spoons, 2 flags)
Benambra (Omeo District FL) - 1999-2000
Imperials (Sunraysia FL) - 2012-2013
Orbost (East Gippsland FL) - 1997-1998
Portarlington (Bellarine FL) - 1991-1992
West Augusta (Spencer Gulf FL) - 1995-1996, 2012-2013

Premiers to wooden spoon:
Bambill (Millewa FL) - 2016-2017 (coming off a threepeat)
Barossa District (Barossa Light & Gawler FL) - 2013-2014
Benambra (Omeo District FL) - 1994-1995, 2000-2001
Donald (North Central FL) - 2006-2007
Millicent (Western Border FL) - 2018-2019
Newcomb (Bellarine FL) - 2007-2008 (did not finish above second last until 2019)
Orbost (East Gippsland FL) - 1996-1997
I'm sure everyone knows but here's a post anyway


South Adelaide SANFL (1964)​

At the end of 1963, the Panthers’ ugly post-World War II rap sheet read: 19 seasons, 12 wooden spoons, five second-last finishes, 12 senior coaches churned through and zero finals.
Twelve months later, South was on top of the world, with legendary player-coach Neil Kerley masterminding the SANFL’s most famous rags-to-riches premiership miracle.
Kerley introduced discipline, fitness and belief to the long-time strugglers, flagless since 1935 when Magpie great Vic Johnson headed south and conjured a similar bottom-to-top turnaround.
Kerley blamed himself for going too defensive when South lost to Port by one point in the 1964 prelim after frittering away a 32-point three-quarter-time lead.
Painful lesson learnt, the Panthers strangled Fos Williams’ powerhouse Magpies in the grand final a fortnight later, restricting them to 0.10 in the first half and triumphing handsomely by 27 points – still South’s most recent pennant.
“1964 was special … bottom to top and beating Port, that was the ultimate,” Kerley said.
 
South Adelaide SANFL (1964)
At the end of 1963, the Panthers’ ugly post-World War II rap sheet read: 19 seasons, 12 wooden spoons, five second-last finishes, 12 senior coaches churned through and zero finals.
Twelve months later, South was on top of the world, with legendary player-coach Neil Kerley masterminding the SANFL’s most famous rags-to-riches premiership miracle.
Kerley introduced discipline, fitness and belief to the long-time strugglers, flagless since 1935 when Magpie great Vic Johnson headed south and conjured a similar bottom-to-top turnaround.
Kerley blamed himself for going too defensive when South lost to Port by one point in the 1964 prelim after frittering away a 32-point three-quarter-time lead.
Painful lesson learnt, the Panthers strangled Fos Williams’ powerhouse Magpies in the grand final a fortnight later, restricting them to 0.10 in the first half and triumphing handsomely by 27 points – still South’s most recent pennant.
“1964 was special … bottom to top and beating Port, that was the ultimate,” Kerley said.
That would have been the Second Semi-final, I'd say!
 
This is an amazing list Connor7395, it's incredible how many players have been both Demons and Saints in their careers.

Some teams tend to exchange players more than others, even among the newer expansion clubs. For example in the 28 years of the Fremantle Dockers they have had a lot of players who joined from North Melbourne, or who would leave for the Kangaroos after a stint at Fremantle. There have also been quite a few Dockers who also played for Melbourne and Sydney.

Collingwood and Richmond traded a lot of players back in the 1980s so little wonder they appear. I noticed Hawthorn and St Kilda on the list and remember in the early 1990s a number of Hawthorn players departing for St Kilda. Although not on the list, Fitzroy and Hawthorn also exchanged quite a few players in the early 1990s.

At the other end of the scale, of the Victorian clubs and Sydney/South Melbourne, are there any teams where players representing both are remarkably few in number? One that came to mind is Hawthorn and Collingwood. There's Tom Mitchell now who was traded to the Magpies by the Hawks at the end of 2022, and back in the mid-late 1990s ex-Hawk Dermott Brereton had a 1 year stint at Collingwood in 1995 to finish his career after a failed season at Sydney in 1994; while Alex McDonald, Hawthorn's No 1 draft pick from 1988 left the Hawks for the Magpies at the end of the 1995 season and played for Collingwood from 1996-1999. But apart from that I'm struggling to name any other players who represented both Collingwood and Hawthorn in their careers.
Late bump. I can give you Bo Nixon who played three games for Collingwood in 2004 before going to Hawthorn where he played once in 05. Hawks fans might be most fond of him because of the trade that got him there. The Hawks traded picks 10 and 37 to the Magpies for Nixon and Pick 7. The Hawks used that selection on Jordan Lewis while the Magpies squandered on the 27 game Chris Egan. This is one of the rare trades that saw the player AND pick upgrade go to the same team. I believe this was three years before the AFL permitted straight pick swaps without involving a player, so I presume Nixon was thrown in to facilitate the trade.
 

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Can anyone add to this list?

100 GAMES FOR TWO CLUBS IN TWO SEPARATE MAJOR LEAGUES


Darrel Baldock 119 St. Kilda VFL 1962-1968; 158 Latrobe NWFU 1959-1961, 1969-1973
Malcolm Blight 152 Woodville SANFL 1968-1973, 1983-1985; 178 North Melbourne VFL 1974-1982
Barry Cable 225 Perth WAFL 1962-1969, 1971-1973; 115 North Melbourne VFL 1970, 1974-1977
Neil Conlan 104 Glenorchy TFL 1953-1958; 105 Devonport NTFL 1959-1966
Polly Farmer 176 East Perth WAFL 1953-1961; 101 Geelong VFL 1962-1967
Brad Hardie 140 South Fremantle WAFL 1979-1984; 101 Brisbane Bears VFL 1987-1991
Syd Jackson 104 East Perth WAFL 1963-1967; 136 Carlton VFL 1969-1976
Peter Jago 122 Claremont WAFL 1949-1956; 107 Longford NTFA 1957-1962
Andrew Jarman 141 North Adelaide SANFL 1983-1989; 110 Adelaide AFL 1991-1996
Darren Jarman 117 North Adelaide SANFL 1985-1990; 109 Hawthorn AFL 1991-1995; 121 Adelaide AFL 1996-2001
Bob Johnson 140 Melbourne VFL 1954-1961; 106 East Fremantle WAFL 1962-1966
Stephen Kernahan 116 Glenelg SANFL 1981-1985; 251 Carlton VFL/AFL 1986-1997
Dwayne Lamb 190 Subiaco WAFL 1980-1986, 1989, 1993-1996; 151 West Coast AFL 1987-1994
Chris McDermott 227 Glenelg SANFL 1981-1996; 117 Adelaide AFL 1991-1996
Tony McGuinness 103 Glenelg SANFL 1981-1985, 1998; 109 Footscray VFL 1986-1990; 113 Adelaide AFL 1991-1996
Graham Melrose 140 East Fremantle WAFL 1967-1974; 111 North Melbourne VFL 1975-1979
Mick Nolan 107 North Melbourne VFL 1973-1980; 103 Mayne QAFL 1981-1986
John Platten 113 Central Districts SANFL 1981-1985, 1998; 258 Hawthorn VFL/AFL 1986-1998
Maurice Rioli 168 South Fremantle WAFL 1975-1981, 1988-1990; 118 Richmond VFL 1982-1987
Barry Round 135 Footscray VFL 1969-1975; 193 South/Sydney VFL 1976-1985; 110 Williamstown VFA 1986-1991
Stuart Spencer 122 Melbourne VFL 1950-1956; 161 Clarence TFL 1957-1963
Mark Williams 115 Port Adelaide SANFL 1979-1980, 1990-1992; 135 Collingwood VFL 1981-1986
 
Or how about this list?


100 GOALS IN A SEASON FOR TWO CLUBS IN TWO SEPARATE MAJOR LEAGUES

Paul Angelis
100 Waverley (VFA, Div 2) 1980
139 Ainslie (ACTAFL) 1984
123 North Shore (NSWAFL) 1988

Simon Beasley
119 Swan Districts (WAFL) 1981
105 Footscray (VFL) 1985

Malcolm Blight
103 North Melbourne (VFL) 1982
126 Woodville (SANFL) 1985

Peter Hudson
110 New Norfolk (TFL) 1965
103 New Norfolk (TFL) 1966
125 Hawthorn (VFL) 1968
120 Hawthorn (VFL) 1969
146 Hawthorn (VFL) 1970
150 Hawthorn (VFL) 1971
133 Glenorchy (TFL) 1976
110 Hawthorn (VFL) 1977
158 Glenorchy (TFL) 1978
179 Glenorchy (TFL) 1979

George Moloney
109 Geelong (VFL) 1932
129 Claremont (WAFL) 1940
108 Claremont (WAFL) 1941

Bob Pratt
109 South Melbourne (VFL) 1933
150 South Melbourne (VFL) 1934
103 South Melbourne (VFL) 1935
183 Coburg (VFA) 1941

Jack Titus
100 Richmond (VFL) 1940
119 Coburg (VFA) 1945

Ron Todd
120 Collingwood (VFL) 1938
121 Collingwood (VFL) 1939
188 Williamstown (VFA) 1945
114 Williamstown (VFA) 1946
 
Another list which may or may not be incomplete

FAIREST AND BEST AWARD WINNERS IN TWO SEPARATE MAJOR LEAGUES


Malcolm Blight
Magarey Medal (SANFL) Woodville 1972
Brownlow Medal (VFL) North Melbourne 1978

Nathan Buckley
Magarey Medal (SANFL) Port Adelaide 1992
Brownlow Medal (AFL) Collingwood 2003

Haydn Bunton
Brownlow Medal (VFL) Fitzroy 1931, 1932, 1935
Sandover Medal (WAFL) Subiaco 1938, 1939, 1941

Terry Cashion
Tasman Shields Trophy (NFTA) Longford 1948, 1950, 1951
Leitch Medal (TFL) Sandy Bay 1953

Albert Collier
Brownlow Medal (VFL) Collingwood 1929
Leitch Medal (TFL) Cananore 1931

Des Fothergill
Brownlow Medal (VFL) Collingwood 1940
Recorder Cup (VFA) Williamstown 1941

Pat Hartnett
Leitch Medal (TFL) Cananore 1932
Recorder Cup (VFA) Brighton 1939

Sam Mitchell
Liston Trophy (VFL) Box Hill 2002
Brownlow Medal (AFL) Hawthorn 2012

Fred Odgers
Cheel Medal (NWFU) Penguin 1924
Tasman Shields Trophy (North Launceston) 1927

John Platten
Magarey Medal (SANFL) Central Districts 1984
Brownlow Medal (VFL) Hawthorn 1987

Max Pontifex
Magarey Medal (SANFL) West Torrens 1932
Tasman Shields Trophy (NTFA) City South 1938

Matt Priddis
Sandover Medal (WAFL) Subiaco 2006
Brownlow Medal (AFL) West Coast 2014

Barry Round
Brownlow Medal (VFL) South Melbourne 1981
Liston Trophy (VFA) Williamstown 1987


NB: edited and amended in conjunction with the post below by the-croucher
 
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Another list which may or may not be incomplete

FAIREST AND BEST AWARD WINNERS IN TWO SEPARATE MAJOR LEAGUES


Malcolm Blight
Magarey Medal (SANFL) Woodville 1972
Brownlow Medal (VFL) North Melbourne 1978

Nathan Buckley
Magarey Medal (SANFL) Port Adelaide 1992
Brownlow Medal (AFL) Collingwood 2003

Haydn Bunton
Brownlow Medal (VFL) Fitzroy 1931, 1932, 1935
Sandover Medal (WAFL) Subiaco 1938, 1939, 1941

Terry Cashion
Hec Smith Medal (NFTA) Longford 1948, 1950, 1951
Leitch Medal (TFL) Sandy Bay 1953

Albert Collier
Brownlow Medal (VFL) Collingwood 1929
Leitch Medal (TFL) Cananore 1931

Des Fothergill
Brownlow Medal (VFL) Collingwood 1940
Recorder Cup (VFA) Williamstown 1941

Sam Mitchell
Liston Trophy (VFL) Box Hill 2002
Brownlow Medal (AFL) Hawthorn 2012

John Platten
Magarey Medal (SANFL) Central Districts 1984
Brownlow Medal (VFL) Hawthorn 1987

Max Pontifex
Magarey Medal (SANFL) West Torrens 1932
Tasman Shield (TFL) City South 1938

Matt Priddis
Sandover Medal (WAFL) Subiaco 2006
Brownlow Medal (AFL) West Coast 2014

Barry Round
Brownlow Medal (VFL) South Melbourne 1981
Liston Trophy (VFA) Williamstown 1987

Bryan Waters
Liston Trophy (VFA) Dandenong 1959
Wander Medal (NWFU) Latrobe 1968
Add
Fred Odgers
Cheel Medal (NWFU) Penguin 1924
Tasman Shields Trophy (North Launceston) 1927

Pat Hartnett
Leitch Medal (TFL) Cananore 1932
Recorder Cup (VFA) Brighton 1939

Delete
Bryan Waters
..he did won the Liston Trophy, but Brian Waters (different person) won the Wander Medal.

Amend
Terry Cashion won Tasman Shields Trophy (NTFA B&F wasn't renamed Hec Smith Medal until 1966)
Max Pontifex's Tasman Shields Trophy in 1938 was in the NTFA, not TFL.
 
Imagine there is an alternate Earth in another dimension where everything is the same, except for one thing. In 1994, the year the AFL introduced a Top 8 which involved two preliminary finals, something minor skewed in the space/time continuum between the two parallel dimensions and from this point on, the results of the AFL preliminary finals in the alternate Earth was the inverse of our Earth, resulting in a different Grand Final each year.

So what would be the alternate grand final match-ups on parallel Earth have been?

1994: Melbourne vs North Melbourne
1995: North Melbourne vs Richmond
1996: Essendon vs. Brisbane Bears
1997: North Melbourne vs. Bulldogs
1998: Bulldogs vs. Melbourne
1999: Essendon vs. Brisbane Lions
2000: Carlton vs. North Melbourne
2001: Hawthorn vs. Richmond
2002: Port Adelaide vs. Adelaide
2003: Port Adelaide vs. Sydney
2004: St Kilda vs. Geelong
2005: Adelaide vs. St Kilda
2006: Adelaide vs. Fremantle
2007: Collingwood vs. North Melbourne
2008: St Kilda vs. Bulldogs
2009: Bulldogs vs. Collingwood
2010: Geelong vs. Bulldogs
2011: Hawthorn vs. West Coast
2012: Collingwood vs. Adelaide
2013: Geelong vs. Sydney
2014: Port Adelaide vs. North Melbourne
2015: Fremantle vs. North Melbourne
2016: Geelong vs. GWS
2017: Geelong vs. GWS
2018: Melbourne vs. Richmond
2019: Geelong vs. Collingwood
2020: Brisbane Lions vs. Port Adelaide
2021: Geelong vs. Port Adelaide
2022: Collingwood vs. Brisbane Lions
2023: GWS vs. Carlton
 
Premierships continue to be elusive for I name players, with North Melbourne's Steven Icke way back in 1977 the last example.
There is only one other I surnamed player who played in a premiership side — John V. Incoll, who played in two premierships for Collingwood as far back as 1902 and 1903.

There are four I surnamed players who played for a runner-up team or in a premiership side during the season:
  1. Dean Irving did play for West Coast in the 1991 Grand Final, and played one game in their 1992 premiership year
  2. Warwick Irwin played for Collingwood in the 1981 Grand Final
  3. Andrew Ireland played for the Magpies in three Grand Finals and one Replay between 1977 and 1980
    1. I recall watching the 1980 Grand Final and seeing Ireland thrashed by David Cloke, who could have had ten goals had he not missed several sitters
  4. Graham Ion played for Footscray in the 1961 Grand Final
 
There is only one other I surnamed player who played in a premiership side — John V. Incoll, who played in two premierships for Collingwood as far back as 1902 and 1903.

There are four I surnamed players who played for a runner-up team or in a premiership side during the season:
  1. Dean Irving did play for West Coast in the 1991 Grand Final, and played one game in their 1992 premiership year
  2. Warwick Irwin played for Collingwood in the 1981 Grand Final
  3. Andrew Irelandplayed for the Magpies in three Grand Finals and one Replay between 1977 and 1980
    1. I recall watching the 1980 Grand Final and seeing Ireland thrashed by David Cloke, who could have had ten goals had he not missed several sitters
  4. Graham Ion played for Footscray in the 1961 Grand Final
As well as Icke and Incoll, Alby Ingleman (Carlton 1907) and Vince Irwin (Essendon 1923) were premiership players. Barry Ion played with his brother (Graham) in the 1961 Grand Final. Anthony Ingerson (Melbourne 2000) was another in a losing side.
 
Brothers Jim and Phil Krakouer were recruited by North Melbourne from WAFL powerhouse Claremont, and were stars for the Kangaroos from 1982-1989 inclusive. What isn't commonly known is that there was a lesser-known Krakouer brother Andrew, who joined North for 1989 but only had a fleeting career. This meant that there were three Krakouer brothers playing at North in 1989, but never in the same team at once and Jim and Phil departed the Kangaroos for St Kilda and Footscray respectively at the end of the year, leaving only Andrew at the Roos for 1990. Interestingly, Andrew Krakouer's last two games for North and of his career would be against his older brothers' two new teams, but neither the Saints or Dogs teams those days contained Jim or Phil.

Some brothers play their entire careers for the same team, some never play for the same team, sometimes they start at the same club and one brother transfers away later on (such as the Madden brothers and Voss brothers), some start at different clubs but finish at the same team (like the Stevens brothers Anthony and Michael at North Melbourne in 2003/2004) and some cross paths and play together mid-career, like the Rocca brothers at Collingwood from 1997-2000, although one seldom sees this situation.

The case of Jim and Phil Krakour playing for the same team but departing for different rival clubs at the same time is rare, but not unique. Justin and Michael Pickering were good players for the struggling Richmond in the late 1980s and early 1990s, but the brothers both departed the Tigers at the end of the 1991 season, joining the Bulldogs and Melbourne respectively. A decade later the Wakelin twins Shane and Daryl left St Kilda following the 2000 season and joined Collingwood and Port Adelaide respectively, playing out their careers at separate clubs in the 2000s.

If anyone knows any other examples like the Krakouer, Pickering and Wakelin brothers who left the club they played at together at the same time and transferred to different rival teams, please post them.
 
If anyone knows any other examples like the Krakouer, Pickering and Wakelin brothers who left the club they played at together at the same time and transferred to different rival teams, please post them.
Paul and Shane Morwood both played for Sydney in 1982, before crossing to St Kilda and Collingwood respectively in 1983.
In Paul's case, his move was famous (infamous) because he initially played for the Saints without a clearance. This was a significant factor in the then VFL being forced to change its rules. Along with Silvio Foschini, who also transferred to St Kilda from the Swans, Morwood and St Kilda were able to establish in court that the leagues player transfer rules were a restraint of trade.
The Morwoods are also interesting in the context of this thread in that there was a third brother -Tony - who was at Sydney at the same time as Paul and Shane. Tony remained at Sydney for his entire 229 game career, retiring in 1989.

Geoff and Gary Ablett (Snr) both played for Hawthorn in 1982 before leaving the Club at the end of that season. Geoff played for St Kilda in 1983. Gary also played for the Saints in 1983 - unfortunately for St Kilda, he played for the Myrtleford Saints in the Ovens & Murray league before moving to Geelong in 1984.
Again there was a third Ablett brother, Kevin. Kevin played at Hawthorn alongside Geoff from 1977 - 1980 before moving to Richmond. The brothers were re-united when Geoff moved again to Richmond in 1984. Finally, Kevin and Gary played a season together when Kevin finished his career at Geelong in 1985.
None of this maybe meets the strict definition of the thread, because never did two brothers move to different league clubs the same season, but I reckon it is still interesting given the fame of the family and the multiple cross-overs.
 
Ryan Gamble played consecutive games for himself between the same two clubs - on both sides. Has anyone heard of another player achieving similar?

Game 24 - round 13, 2010 for Geelong against St Kilda
Game 25 - round 1, 2011 for St Kilda against Geelong

Was intrigued by this about thinking of Caleb Poulter, whose last game for Collingwood was against the Bulldogs. Unfortunately, his first game against Collingwood was his second game for the Bulldogs, after playing against Freo the week before.
 
Examples of teams who went from wooden spoon to premiers in the space of two years (from footy.fandom.com):

Wooden spoon to premiers:
Portarlington (Bellarine FL) - 1991-1992
You actually left off Portarlington in the Premiers to wooden spoon category. They won the flag in 1994 and dropped to last in 1995.
Their story since is really something to behold, and an unfortunate cycle of poor performances on the field.

In the 27 completed seasons since that 1994 premiership, Port has finished in the bottom two in 24 of those seasons. Their best performance has been back-to-back 7th-place finishes in 2007 and 2008. They are currently on a 68-game losing streak, which is the second largest in the state.

However, they have always been really strong off the field, have won numerous junior premierships, and have a solid supporter base and sponsor base. I think it's simply the tyranny of distance combined with the sustained low finishes making it hard to attract recruits.

2024 is the club's 150th season, and with a big points allowance from the league, they've loaded up with three ex-AFL players: Teia Miles, Connor Menadue and Jarryd Cachia. I genuinely hope they win at least a few games this year. The league has a sense of theatre in scheduling their opening match at home to fellow perennial cellar-dwellers Newcomb.

 

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