History
The club was formed in 1891 and after having success in the Melbourne Districts Association League they were one of two teams admitted into the VFA in 1929, the other being Sandringham. With former Essendon star and future Carlton coach Frank Maher in charge they won a premiership in just their second season with a 9 point win over Northcote in a very spiteful game, 9.6 (60) to 7.9 (51). The game had erupted into full scale violence during the last term when a Northcote defender elbowed an Oakleigh forward in the face and an all in brawl, involving a number of spectators as well as most players, ensued. Under the rules of the time, Oakleigh would have been able to challenge Northcote the following week if they had lost this game as they had finished as minor premiers after the home and away matches preceding the finals series. The two sides met once more in the Grand Final the following year and Oakleigh again got the better of Northcote, winning by 3 points despite kicking inaccurately, 10.14 (74) to 11.5 (71).
It would be the last time the club saw finals football until 1949 when they made it all the way to the Grand Final before losing when a Williamstown player kicked a goal with only seconds to play to put his team in front. They earned the minor premiership the following season and outplayed Port Melbourne to win their third premiership. In 1952 the teams met again in the Grand Final and Oakleigh won comfortably.
Another drought ensued and Oakleigh didn't make the finals again until 1959. They won their 5th premiership in 1960 despite not being able to play at their home ground which was having resurfacing work.
In 1966 Oakleigh were demoted to the second division by finishing bottom of the first division but won the second division premiership by defeating Geelong West in the Grand Final in 1967 and returned to the top flight for 1968. In the following decade they made consecutive Grand Final appearances in 1972, 1973 and 1974. The 1972 grand final saw them defeat Dandenong in a high scoring match, 25.17 (167) to 18.15 (123). In 1976 they were relegated again and remained in the second division, losing a number of grand finals along the way, until 1988 when they finally won the premiership. At the end of this season, the two division format was scrapped and all of the existing VFA clubs were merged into one competition for the following season.
Oakleigh struggled to make an impact after this and never managed to move far off the bottom of the ladder again. They decided to leave the VFA after the 1994 season, when the VFA was restructured, in order to create an Under-18 feeder club for another VFA team, local rivals Springvale.
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