The 2019–20 Wessex Football League season (known as the Sydenhams Football League (Wessex) for sponsorship reasons) was the 33nd in the history of the Wessex Football League since its establishment in 1986
Premier Division
Fixtures
| Date | Home | Time/Results | Away |
|---|---|---|---|
AFC Stoneham  |  Poppies | ||
Team Solent  | Poppies | ||
| Poppies |  Brockenhurst | ||
| Poppies |  Fleet Town | ||
Cowes Sports  | Poppies | ||
Christchurch FC  | Poppies | ||
| Poppies |  Tadley Calleva FC | ||
Horndean  | Poppies | ||
| Poppies |  Bashley | ||
Baffins Milton Rovers  | Poppies | ||
| Poppies | Christchurch FC | ||
| Brockenhurst | Poppies | ||
| Poppies |  Fareham Town |