Vermont were formed in late 1919 and played their first season in 1920 in the Reporter District FL defeating Warrandyte in their first game.
The lack of premiership success continued and the club was forced by the Great Depression to spend the years 1932 to 1934 as a merged entity with Mitcham.
Upon separation in 1935, Vermont went into recess for the season due to internal arguments preventing an application for affiliation.
In 1936, Vermont joined the Federal FL for a season and had appointed former Collingwood champion Charlie Pannam as coach.
This lasted for two years only as World War II started to bite and Vermont went into recess until 1948.
The Eagles bounced back to win the B Grade premiership over East Burwood, but they were not promoted as they then decided to follow Mitcham and Ringwood to the Croydon Ferntree Gully league.
They built up and made the finals for the first time in the league in 1962 – the same year the CFTGFL changed its name to the Eastern Districts FL.