| 1 | Tue 17 Sep | 103-4 v Woodley UnitedWoodley United 4-3 Windsor | Combined Counties League Division One | 1 |
| 2 | Sat 21 Sep | 114-1 v Rising Ballers KensingtonRising Ballers Kensington 1-4 Windsor | Combined Counties League Division One | 2 |
| 3 | Tue 24 Sep | 114-1 v MoleseyMolesey 1-4 Windsor | Cherry Red Records Premier Challenge Cup First Round | 1 |
| 4 | Fri 15 Nov | 111-2 v Woodley UnitedWindsor 1-2 Woodley United | Combined Counties League Division One | 1 |
| 5 | Fri 22 Nov | 103-2 v Chalfont St PeterWindsor 3-2 Chalfont St Peter | Combined Counties League Division One | 1 |
| 6 | Fri 20 Dec | 71-2 v Rising Ballers KensingtonWindsor 1-2 Rising Ballers Kensington | Combined Counties League Division One | 1 |
| 7 | Fri 17 Jan | 103-4 v Oxhey JetsWindsor 3-4 Oxhey Jets | Combined Counties League Division One | 1 |
| 8 | Tue 22 Apr | 72-2 v Eversley & CaliforniaWindsor 2-2 Eversley & California | Combined Counties League Division One | 1 |
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