| 1 | Tue 1 Jul | 22-2 v Retford UnitedRetford United 2-2 Boston Town | Friendly |
| 2 | Sat 5 Jul | 84-1 v March Town UnitedBoston Town 4-1 March Town United | Friendly |
| 3 | Sat 2 Aug | 42-0 v Kimberley Miners WelfareBoston Town 2-0 Kimberley Miners Welfare | Emirates FA Cup Extra Preliminary Round |
| 4 | Sat 9 Aug | 42-1 v Ashby IvanhoeAshby Ivanhoe 1-2 Boston Town | United Counties League Premier Division North |
| 5 | Tue 12 Aug | 42-1 v Newark TownBoston Town 2-1 Newark Town | United Counties League Premier Division North |
| 6 | Sat 16 Aug | 20-0 v Newark and Sherwood UnitedNewark and Sherwood United 0-0 Boston Town | Emirates FA Cup Preliminary Round |
| 7 | Tue 19 Aug | 24-1 v Newark and Sherwood UnitedBoston Town 4-1 Newark and Sherwood United | Emirates FA Cup Preliminary Round Replay |
| 8 | Sat 30 Aug | 12 1-1 v Sporting KhalsaBoston Town 1-1 Sporting Khalsa | Emirates FA Cup First Qualifying Round |
| 9 | Sat 6 Sep | 122-0 v Hucknall TownBoston Town 2-0 Hucknall Town | Sports Ground Development UCL Cup |
| 10 | Sat 20 Sep | 27-0 v BlackstonesBoston Town 7-0 Blackstones | United Counties League Premier Division North |
| 11 | Sat 18 Oct | 123-4 v Clay Cross TownBoston Town 3-4 Clay Cross Town | United Counties League Premier Division North |
| 12 | Sat 25 Oct | 4 0-2 v Gresley RoversGresley Rovers 2-0 Boston Town | United Counties League Premier Division North |
| 13 | Sat 1 Nov | 4 3-3 v MoultonMoulton 3-3 Boston Town | Sports Ground Development UCL Cup Second Round |
| 14 | Sat 8 Nov | 82-2 v Belper UnitedBelper United 2-2 Boston Town | United Counties League Premier Division North |
| 15 | Tue 11 Nov | 26-0 v Harrowby UnitedBoston Town 6-0 Harrowby United | United Counties League Premier Division North |
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