| 1 | Sat 10 Aug | 11-4 v Virginia WaterHilltop 1-4 Virginia Water | Combined Counties League Premier Division North |
| 2 | Sat 24 Aug | 13-2 v Harefield UnitedHilltop 3-2 Harefield United | Combined Counties League Premier Division North |
| 3 | Mon 26 Aug | 10-3 v HolyportHolyport 3-0 Hilltop | Combined Counties League Premier Division North |
| 4 | Sat 31 Aug | 10-0 v Risborough RangersRisborough Rangers 0-0 Hilltop | Combined Counties League Premier Division North |
| 5 | Sat 7 Sep | 11-0 v Ardley UnitedHilltop 1-0 Ardley United | Combined Counties League Premier Division North |
| 6 | Tue 10 Sep | 11-1 v Bedfont SportsBedfont Sports 1-1 Hilltop | Combined Counties League Premier Division North |
| 7 | Wed 18 Sep | 12-1 v Wallingford & CrowmarshHilltop 2-1 Wallingford & Crowmarsh | Combined Counties League Premier Division North |
| 8 | Sat 21 Sep | 10-3 v Wokingham TownWokingham Town 3-0 Hilltop | Combined Counties League Premier Division North |
| 9 | Tue 24 Sep | 11-4 v Epsom & EwellEpsom & Ewell 4-1 Hilltop | Cherry Red Records Premier Challenge Cup First Round |
| 10 | Sat 28 Sep | 10-4 v BurnhamHilltop 0-4 Burnham | Combined Counties League Premier Division North |
| 11 | Tue 1 Oct | 212-0 v Berks CountyBerks County 0-2 Hilltop | Combined Counties League Premier Division North |
| 12 | Sat 5 Oct | 124-1 v British AirwaysBritish Airways 1-4 Hilltop | Combined Counties League Premier Division North |
| 13 | Sat 12 Oct | 121-3 v Egham TownHilltop 1-3 Egham Town | Combined Counties League Premier Division North |
| 14 | Tue 22 Oct | 1 1-2 v Harefield UnitedHarefield United 2-1 Hilltop | Middlesex Challenge Cup First Round |
| 15 | Sat 26 Oct | 12-1 v Wallingford & CrowmarshWallingford & Crowmarsh 1-2 Hilltop | Combined Counties League Premier Division North |
| 16 | Sat 9 Nov | 10-5 v Windsor & EtonWindsor & Eton 5-0 Hilltop | Isuzu FA Vase Second Round |
| 17 | Tue 3 Dec | 120-11 v Egham TownEgham Town 11-0 Hilltop | Combined Counties League Premier Division North |
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