| 1 | Tue 1 Jul | 12-2 v Retford UnitedRetford United 2-2 Boston Town | Friendly |
| 2 | Sat 5 Jul | 14-1 v March Town UnitedBoston Town 4-1 March Town United | Friendly |
| 3 | Tue 8 Jul | 12-1 v Louth TownLouth Town 1-2 Boston Town | Friendly |
| 4 | Tue 15 Jul | 12-2 v Boston UnitedBoston Town 2-2 Boston United | Friendly |
| 5 | Sat 26 Jul | 12-2 v Heanor TownBoston Town 2-2 Heanor Town | United Counties League Premier Division North |
| 6 | Sat 2 Aug | 12-0 v Kimberley Miners WelfareBoston Town 2-0 Kimberley Miners Welfare | Emirates FA Cup Extra Preliminary Round |
| 7 | Sat 9 Aug | 12-1 v Ashby IvanhoeAshby Ivanhoe 1-2 Boston Town | United Counties League Premier Division North |
| 8 | Tue 12 Aug | 12-1 v Newark TownBoston Town 2-1 Newark Town | United Counties League Premier Division North |
| 9 | Sat 16 Aug | 10-0 v Newark and Sherwood UnitedNewark and Sherwood United 0-0 Boston Town | Emirates FA Cup Preliminary Round |
| 10 | Tue 19 Aug | 14-1 v Newark and Sherwood UnitedBoston Town 4-1 Newark and Sherwood United | Emirates FA Cup Preliminary Round Replay |
| 11 | Sat 30 Aug | 11-1 v Sporting KhalsaBoston Town 1-1 Sporting Khalsa | Emirates FA Cup First Qualifying Round |
| 12 | Tue 2 Sep | 10-2 v Sporting KhalsaSporting Khalsa 2-0 Boston Town | Emirates FA Cup First Qualifying Round Replay |
| 13 | Sat 6 Sep | 12-0 v Hucknall TownBoston Town 2-0 Hucknall Town | Sports Ground Development UCL Cup |
| 14 | Sat 13 Sep | 12-1 v Hucknall TownHucknall Town 1-2 Boston Town | United Counties League Premier Division North |
| 15 | Tue 16 Sep | 17-2 v Wisbech TownBoston Town 7-2 Wisbech Town | United Counties League Premier Division North |
| 16 | Sat 20 Sep | 17-0 v BlackstonesBoston Town 7-0 Blackstones | United Counties League Premier Division North |
| 17 | Sat 27 Sep | 13-1 v Melton TownBoston Town 3-1 Melton Town | United Counties League Premier Division North |
| 18 | Tue 30 Sep | 12-1 v Sherwood CollierySherwood Colliery 1-2 Boston Town | Sports Ground Development UCL Cup First Round |
| 19 | Sat 4 Oct | 15-0 v Harrowby UnitedHarrowby United 0-5 Boston Town | United Counties League Premier Division North |
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