| 1 | Sat 12 Sep | 19 1-3 v NorthwoodNorthwood 3-1 Maidenhead Town | FA Vase Second Qualifying Round |
| 2 | Sat 19 Sep | 152-3 v LangleyMaidenhead Town 2-3 Langley | Combined Counties League Division One |
| 3 | Tue 22 Sep | 19 1-5 v BelstoneBelstone 5-1 Maidenhead Town | Combined Counties League Division One |
| 4 | Wed 30 Sep | 19 2-3 v Brook HouseMaidenhead Town 2-3 Brook House | Combined Counties League Division One |
| 5 | Sat 3 Oct | 19 3-3 v PFC Victoria LondonMaidenhead Town 3-3 PFC Victoria London | Combined Counties League Division One |
| 6 | Tue 6 Oct | 192-1 v Brook HouseBrook House 1-2 Maidenhead Town | CCL Division One Challenge Cup First Round |
| 7 | Sat 24 Oct | 192-1 v Spartans YouthMaidenhead Town 2-1 Spartans Youth | Combined Counties League Division One |
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