| 1 | Fri 2 Aug | 123-2 v Brook HouseWindsor 3-2 Brook House | Combined Counties League Division One |
| 2 | Tue 6 Aug | 150-3 v Penn & Tylers GreenWindsor 0-3 Penn & Tylers Green | Combined Counties League Division One |
| 3 | Sat 10 Aug | 75-2 v FC Deportivo GaliciaFC Deportivo Galicia 2-5 Windsor | Combined Counties League Division One |
| 4 | Sat 17 Aug | 111-0 v Colliers Wood UnitedColliers Wood United 0-1 Windsor | Combined Counties League Division One |
| 5 | Tue 20 Aug | 111-1 v Spartans YouthWindsor 1-1 Spartans Youth | Combined Counties League Division One |
| 6 | Fri 23 Aug | 70-0 v PFC Victoria LondonWindsor 0-0 PFC Victoria London | Combined Counties League Division One |
| 7 | Mon 26 Aug | 90-1 v Windsor & EtonWindsor & Eton 1-0 Windsor | Combined Counties League Division One |
| 8 | Fri 30 Aug | 173-2 v Staines & Lammas (Middlesex)Windsor 3-2 Staines & Lammas (Middlesex) | Combined Counties League Division One |
| 9 | Tue 3 Sep | 90-6 v Brook HouseBrook House 6-0 Windsor | Combined Counties League Division One |
| 10 | Fri 6 Sep | 122-0 v LangleyWindsor 2-0 Langley | Combined Counties League Division One |
| 11 | Tue 10 Sep | 114-2 v BurnhamWindsor 4-2 Burnham | Berks and Bucks County Cup First Round |
| 12 | Fri 13 Sep | 140-3 v WestsideWindsor 0-3 Westside | Combined Counties League Division One |
| 13 | Tue 24 Sep | 174-1 v MoleseyMolesey 1-4 Windsor | Cherry Red Records Premier Challenge Cup First Round |
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