Osborne is set to celebrate its senior 1985, 1995 and 2005 premiership triumphs this weekend.
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And while premiership reunions have been commonplace during the Cats golden era of the past 25 years, the 1985 flag holds special significance.
It was the season the Cats snapped a 24-year premiership drought and claimed their first Hume league flag since joining the competition in 1970.
The perennial powerhouse has since won flags in 1991, 1992, 1994, 1995, 1998, 1999, 2000, 2001, 2005, 2006, 2009 and 2012 to boast one of the most enviable records in country football.
Coached by Phil Cox, the Cats finished full of running in the 1985 decider against Henty to score a 16.11 (107) to 13.10 (88) victory after trailing by nine points with less than 10 minutes remaining.
Cox, who now resides in Adelaide, will make the trek to Osborne on Saturday when it hosts Rand-Walbundrie.
“I remember there was nine minutes remaining and we were nine points down,” Cox said.
“Panic stations started to set in for some of the older officials and supporters who had been waiting almost 25 years for a flag.
“I must admit, I thought we might have blown a golden opportunity also.”
With Osborne looking down and out, Cox said Danny Ryan bobbed up as an unlikely match-winner.
“We had a fresh bloke on the bench in Danny Ryan,” he said.
“With everyone fatigued and just over five minutes remaining, Danny came on and had an instant impact and kicked a goal.
“He ended up having a heap of important touches and we ended up winning by 19 points.”
The 1985 premiership side boasted some classy imports in Cox, Billy Blight, Ray Scott, Kevin Mack, Graham Doswell and Wayne Howie.
But Cox said it was the club’s junior talent in Richard Gleeson, James O’Connell, Max O’Connell, Brent Alexander, Chris Ralston and Leyland Hinch who were also instrumental in the drought breaking flag.
Tony MacTavish led the Cats to the holy grail in 1995 while Michael Buchanan did likewise in 2005.
Osborne will also celebrate its thirds flags in 1985 and 2005 along with its reserve grade flag in 2005.
In other matches, Brock-Burrum and Henty clash in a possible grand final preview while Howlong will start favourites against Jindera.
Murray Magpies will be looking for a big scalp when it hosts CDHBU.
Little should separate Culcairn and Lockhart while the Walla and Holbrook clash should also be a tight encounter.