| 1 | Tue 4 Aug | 211-5 v WembleyWembley 5-1 Maidenhead Town | Combined Counties League Division One |
| 2 | Tue 11 Aug | 214-3 v Shepherd's BushShepherd's Bush 3-4 Maidenhead Town | Combined Counties League Division One |
| 3 | Sat 15 Aug | 211-5 v Berks CountyMaidenhead Town 1-5 Berks County | Combined Counties League Division One |
| 4 | Tue 18 Aug | 251-0 v Spartans YouthSpartans Youth 0-1 Maidenhead Town | Combined Counties League Division One |
| 5 | Sat 22 Aug | 251-1 v London Samurai RoversMaidenhead Town 1-1 London Samurai Rovers | Combined Counties League Division One |
| 6 | Mon 31 Aug | 251-4 v Holmer GreenHolmer Green 4-1 Maidenhead Town | Combined Counties League Division One |
| 7 | Sat 5 Sep | 25-2 v FC Deportivo GaliciaFC Deportivo Galicia 2-5 Maidenhead Town | Combined Counties League Division One |
| 8 | Sat 12 Sep | 251-3 v NorthwoodNorthwood 3-1 Maidenhead Town | FA Vase Second Qualifying Round |
| 9 | Tue 15 Sep | 250-5 v Berks CountyBerks County 5-0 Maidenhead Town | Combined Counties League Division One |
| 10 | Sat 19 Sep | 252-3 v LangleyMaidenhead Town 2-3 Langley | Combined Counties League Division One |
| 11 | Tue 22 Sep | 251-5 v BelstoneBelstone 5-1 Maidenhead Town | Combined Counties League Division One |
| 12 | Sat 26 Sep | 251-3 v Edgware & KingsburyEdgware & Kingsbury 3-1 Maidenhead Town | Combined Counties League Division One |
| 13 | Wed 30 Sep | 252-3 v Brook HouseMaidenhead Town 2-3 Brook House | Combined Counties League Division One |
| 14 | Sat 3 Oct | 253-3 v PFC Victoria LondonMaidenhead Town 3-3 PFC Victoria London | Combined Counties League Division One |
| 15 | Tue 6 Oct | 212-1 v Brook HouseBrook House 1-2 Maidenhead Town | CCL Division One Challenge Cup First Round |
| 16 | Sat 10 Oct | 252-2 v Eagles Land BenficaEagles Land Benfica 2-2 Maidenhead Town | Combined Counties League Division One |
| 17 | Sat 17 Oct | 252-3 v MoleseyMolesey 3-2 Maidenhead Town | Combined Counties League Division One |
| 18 | Sat 24 Oct | 252-1 v Spartans YouthMaidenhead Town 2-1 Spartans Youth | Combined Counties League Division One |
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