| 1 | Wed 29 Jul | 204-0 v Oxhey JetsMaidenhead Town 4-0 Oxhey Jets | Combined Counties League Division One |
| 2 | Sat 1 Aug | 203-3 v Staines & Lammas (Middlesex)Maidenhead Town 3-3 Staines & Lammas (Middlesex) | Combined Counties League Division One |
| 3 | Tue 4 Aug | 201-5 v WembleyWembley 5-1 Maidenhead Town | Combined Counties League Division One |
| 4 | Mon 31 Aug | 201-4 v Holmer GreenHolmer Green 4-1 Maidenhead Town | Combined Counties League Division One |
| 5 | Sat 5 Sep | 205-2 v FC Deportivo GaliciaFC Deportivo Galicia 2-5 Maidenhead Town | Combined Counties League Division One |
| 6 | Sat 12 Sep | 201-3 v NorthwoodNorthwood 3-1 Maidenhead Town | FA Vase Second Qualifying Round |
| 7 | Tue 15 Sep | 200-5 v Berks CountyBerks County 5-0 Maidenhead Town | Combined Counties League Division One |
| 8 | Tue 6 Oct | 202-1 v Brook HouseBrook House 1-2 Maidenhead Town | CCL Division One Challenge Cup First Round |
| 9 | Sat 10 Oct | 202-2 v Eagles Land BenficaEagles Land Benfica 2-2 Maidenhead Town | Combined Counties League Division One |
| 10 | Sat 24 Oct | 202-1 v Spartans YouthMaidenhead Town 2-1 Spartans Youth | Combined Counties League Division One |
| 11 | Sat 31 Oct | 202-2 v Shepherd's BushMaidenhead Town 2-2 Shepherd's Bush | Combined Counties League Division One |
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