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 |
|---|---|---|---|
Poppies  |  Portland United | ||
| Poppies |  Tadley Calleva FC | ||
Alresford Town  | Poppies | ||
Christchurch FC  | Poppies | ||
Baffins Milton Rovers  | Poppies | ||
| Poppies |  Horndean | ||
Team Solent  | Poppies | ||
| Tadley Calleva FC | Poppies | ||
| Poppies | Team Solent | ||
| Poppies |  Fleet Town | ||
Amesbury Town  | Poppies | ||
Bashley  | Poppies | ||
| Poppies |  Shaftesbury FC |