| Competition: | Isle of Man Football League |
| Prevseason: | 2007–08 |
| Nextseason: | 2009–10 |
| Season: | 2008–09 |
The 2008–09 Isle of Man League was the 100th season of Football league on the Isle of Man.
There were two tiers of men's football, consisting 27 clubs, the Sure Mobile Premier League and the CFS Division Two. There were six senior cup competitions – the Manx FA Cup, Railway Cup, Hospital Cup, Woods Cup, Paul Henry Gold Cup and the Charity Shield. Each club had a reserve team in the Isle of Man Football Combination, and they compete in the Junior Cup. There was also the Cowell Cup, an annual Under-19 tournament.
Cup results for 2008–09:[1]
Douglas HSOB 1–1 (3–2 on pens.) St Georges
Peel 0–1 Rushen United
St Georges 2–1 Laxey
Douglas Royal 1–0 Pulrose United
Castletown Metropolitan 4–0 Marown
Castletown Metropolitan 3–1 St Johns United