| 1 | Tue 1 Jul | 142-2 v Retford UnitedRetford United 2-2 Boston Town | Friendly |
| 2 | Sat 5 Jul | 24-1 v March Town UnitedBoston Town 4-1 March Town United | Friendly |
| 3 | Tue 8 Jul | 82-1 v Louth TownLouth Town 1-2 Boston Town | Friendly |
| 4 | Sat 12 Jul | 25-1 v Pinchbeck UnitedPinchbeck United 1-5 Boston Town | Friendly |
| 5 | Sat 26 Jul | 22-2 v Heanor TownBoston Town 2-2 Heanor Town | United Counties League Premier Division North |
| 6 | Sat 16 Aug | 120-0 v Newark and Sherwood UnitedNewark and Sherwood United 0-0 Boston Town | Emirates FA Cup Preliminary Round |
| 7 | Tue 19 Aug | 124-1 v Newark and Sherwood UnitedBoston Town 4-1 Newark and Sherwood United | Emirates FA Cup Preliminary Round Replay |
| 8 | Sat 30 Aug | 81-1 v Sporting KhalsaBoston Town 1-1 Sporting Khalsa | Emirates FA Cup First Qualifying Round |
| 9 | Tue 2 Sep | 110-2 v Sporting KhalsaSporting Khalsa 2-0 Boston Town | Emirates FA Cup First Qualifying Round Replay |
| 10 | Sat 6 Sep | 102-0 v Hucknall TownBoston Town 2-0 Hucknall Town | Sports Ground Development UCL Cup |
| 11 | Sat 13 Sep | 93-1 v Hucknall TownHucknall Town 1-3 Boston Town | United Counties League Premier Division North |
| 12 | Tue 16 Sep | 97-2 v Wisbech TownBoston Town 7-2 Wisbech Town | United Counties League Premier Division North |
| 13 | Sat 20 Sep | 97-0 v BlackstonesBoston Town 7-0 Blackstones | United Counties League Premier Division North |
| 14 | Tue 23 Sep | 91-1 v Deeping RangersDeeping Rangers 1-1 Boston Town | United Counties League Premier Division North |
| 15 | Sat 27 Sep | 23-1 v Melton TownBoston Town 3-1 Melton Town | United Counties League Premier Division North |
| 16 | Tue 30 Sep | 112-1 v Sherwood CollierySherwood Colliery 1-2 Boston Town | Sports Ground Development UCL Cup First Round |
| 17 | Sat 4 Oct | 25-0 v Harrowby UnitedHarrowby United 0-5 Boston Town | United Counties League Premier Division North |
| 18 | Sat 18 Oct | 23-4 v Clay Cross TownBoston Town 3-4 Clay Cross Town | United Counties League Premier Division North |
| 19 | Sat 25 Oct | 20-2 v Gresley RoversGresley Rovers 2-0 Boston Town | United Counties League Premier Division North |
| 20 | Tue 4 Nov | 81-0 v Newark and Sherwood UnitedNewark and Sherwood United 0-1 Boston Town | United Counties League Premier Division North |
| 21 | Sat 8 Nov | 22-2 v Belper UnitedBelper United 2-2 Boston Town | United Counties League Premier Division North |
| 22 | Tue 11 Nov | 146-0 v Harrowby UnitedBoston Town 6-0 Harrowby United | United Counties League Premier Division North |
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