| 1 | Sat 9 Aug 2014 | 2-1 v Sutton UnitedMaidenhead United 2-1 Sutton United | Vanarama Conference South |
| 2 | Sat 6 Sep 2014 | 2-1 v Staines TownStaines Town 1-2 Maidenhead United | Vanarama Conference South |
| 3 | Tue 9 Sep 2014 | 0-1 v FarnboroughMaidenhead United 0-1 Farnborough | Vanarama Conference South |
| 4 | Sat 13 Sep 2014 | 1-4 v St Albans CitySt Albans City 4-1 Maidenhead United | Vanarama Conference South |
| 5 | Sat 20 Sep 2014 | 0-2 v Havant & WaterloovilleMaidenhead United 0-2 Havant & Waterlooville | Vanarama Conference South |
| 6 | Tue 7 Oct 2014 | 6-2 v Weston-super-MareMaidenhead United 6-2 Weston-super-Mare | Vanarama Conference South |
| 7 | Sat 18 Oct 2014 | 2-2 v Concord RangersConcord Rangers 2-2 Maidenhead United | Vanarama Conference South |
| 8 | Sat 25 Oct 2014 | 2-0 v Staines TownMaidenhead United 2-0 Staines Town | Vanarama Conference South |
| 9 | Sat 1 Nov 2014 | 41-1 v WealdstoneWealdstone 1-1 Maidenhead United | Vanarama Conference South |
| 10 | Sat 15 Nov 2014 | 40-4 v Bath CityBath City 4-0 Maidenhead United | Vanarama Conference South |
| 11 | Sat 6 Dec 2014 | 40-4 v Ebbsfleet UnitedMaidenhead United 0-4 Ebbsfleet United | Vanarama Conference South |
| 12 | Sat 20 Dec 2014 | 41-1 v FarnboroughFarnborough 1-1 Maidenhead United | Vanarama Conference South |
| 13 | Fri 26 Dec 2014 | 42-0 v Hayes & Yeading UnitedMaidenhead United 2-0 Hayes & Yeading United | Vanarama Conference South |
| 14 | Sun 28 Dec 2014 | 42-2 v Eastbourne BoroughEastbourne Borough 2-2 Maidenhead United | Vanarama Conference South |
| 15 | Thu 1 Jan 2015 | 41-1 v Hayes & Yeading UnitedHayes & Yeading United 1-1 Maidenhead United | Vanarama Conference South |
| 16 | Sat 24 Jan 2015 | 1-1 v St Albans CityMaidenhead United 1-1 St Albans City | Vanarama Conference South |
| 17 | Sat 7 Feb 2015 | 2-3 v Basingstoke TownBasingstoke Town 3-2 Maidenhead United | Vanarama Conference South |
| 18 | Sat 14 Feb 2015 | 2-0 v Chelmsford CityMaidenhead United 2-0 Chelmsford City | Vanarama Conference South |
| 19 | Tue 17 Feb 2015 | 0-3 v Basingstoke TownMaidenhead United 0-3 Basingstoke Town | Vanarama Conference South |
| 20 | Sat 21 Feb 2015 | 1-1 v Havant & WaterloovilleHavant & Waterlooville 1-1 Maidenhead United | Vanarama Conference South |
| 21 | Sat 28 Feb 2015 | 0-2 v WhitehawkMaidenhead United 0-2 Whitehawk | Vanarama Conference South |
| 22 | Sat 18 Apr 2015 | 1-4 v WealdstoneMaidenhead United 1-4 Wealdstone | Vanarama Conference South |
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