The club continued its affiliation with this league for many decades, even fielding an open age team during the war years.

Cheltenham produced its only Brownlow Medallist in Peter Box who played in the late 1940s, before going to the Footscray Football Club where he became a champion.

The 1960s saw Peter Lucas and Arthur Gooch from Collingwood showing their presence, with Cheltenham being beaten by a kick after the siren against Springvale in the 1960 preliminary final.

The 3rd XVIII went through the season undefeated in 1974 winning the premiership, with Trevor Barker a key player before going to St Kilda the following year.

The 1990s brought back memories of Cheltenham's early years with the club winning 3 senior premierships under coach Barry White in 1992, 1993, and 1995.

The 3rd XVIII were premiers in 1996 and runners up in 1997 under coach Jeff Lyon, who had worked tirelessly recruiting junior players to the club.

Former Richmond and Essendon player Brian Winton took over the coaching duties in 1996 and lead the club to the finals in his first year and then again in 1999.

In 2003 season club stalwart Stephen Kneen took on the enormous task of president, secretary and treasurer all in the same year.

In a big turnaround from previous seasons, the Rosellas finished third with a 14–4 record and in the process won the SFL Division 1 Club Championship.

Ruckman Ewen McKenzie capped off a stellar first season at the club by winning the SFL Division 1 Best and Fairest award.

After missing the finals for the first time in five seasons in 2010, former Melbourne defender Nathan Brown took over the coaching reins and led the Rosellas side back to September action.

In the Elimination Final, Cheltenham defeated preseason flag favourite Chelsea Heights before falling a week later to St Kilda City in the first semifinal.

On the day of the announcement, many friends and family, Cheltenham, and St. Kilda players came to see the unveiling of Jack's name on the side of the pavilion.

Defeating East Malvern and Dingley the seniors made it through to the SFNL Division 1 Grand Final for the first time since in many years.

The grand finale was played at RSEA Park Linton St Moorabbin on a very windy day which made scoring very difficult.