| 1 | Tue 4 Aug | 221-5 v WembleyWembley 5-1 Maidenhead Town | Combined Counties League Division One |
| 2 | Tue 11 Aug | 224-3 v Shepherd's BushShepherd's Bush 3-4 Maidenhead Town | Combined Counties League Division One |
| 3 | Sat 15 Aug | 221-5 v Berks CountyMaidenhead Town 1-5 Berks County | Combined Counties League Division One |
| 4 | Tue 18 Aug | 221-0 v Spartans YouthSpartans Youth 0-1 Maidenhead Town | Combined Counties League Division One |
| 5 | Sat 5 Sep | 225-2 v FC Deportivo GaliciaFC Deportivo Galicia 2-5 Maidenhead Town | Combined Counties League Division One |
| 6 | Sat 12 Sep | 221-3 v NorthwoodNorthwood 3-1 Maidenhead Town | FA Vase Second Qualifying Round |
| 7 | Tue 15 Sep | 220-5 v Berks CountyBerks County 5-0 Maidenhead Town | Combined Counties League Division One |
| 8 | Sat 19 Sep | 222-3 v LangleyMaidenhead Town 2-3 Langley | Combined Counties League Division One |
| 9 | Sat 26 Sep | 221-3 v Edgware & KingsburyEdgware & Kingsbury 3-1 Maidenhead Town | Combined Counties League Division One |
| 10 | Wed 30 Sep | 222-3 v Brook HouseMaidenhead Town 2-3 Brook House | Combined Counties League Division One |
| 11 | Tue 6 Oct | 222-1 v Brook HouseBrook House 1-2 Maidenhead Town | CCL Division One Challenge Cup First Round |
| 12 | Sat 10 Oct | 222-2 v Eagles Land BenficaEagles Land Benfica 2-2 Maidenhead Town | Combined Counties League Division One |
| 13 | Sat 17 Oct | 222-3 v MoleseyMolesey 3-2 Maidenhead Town | Combined Counties League Division One |
| 14 | Sat 24 Oct | 222-1 v Spartans YouthMaidenhead Town 2-1 Spartans Youth | Combined Counties League Division One |
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