| 1 | Tue 1 Jul | 92-2 v Retford UnitedRetford United 2-2 Boston Town | Friendly |
| 2 | Sat 5 Jul | 94-1 v March Town UnitedBoston Town 4-1 March Town United | Friendly |
| 3 | Sat 26 Jul | 142-2 v Heanor TownBoston Town 2-2 Heanor Town | United Counties League Premier Division North |
| 4 | Sat 2 Aug | 92-0 v Kimberley Miners WelfareBoston Town 2-0 Kimberley Miners Welfare | Emirates FA Cup Extra Preliminary Round |
| 5 | Sat 9 Aug | 92-1 v Ashby IvanhoeAshby Ivanhoe 1-2 Boston Town | United Counties League Premier Division North |
| 6 | Tue 12 Aug | 92-1 v Newark TownBoston Town 2-1 Newark Town | United Counties League Premier Division North |
| 7 | Sat 16 Aug | 90-0 v Newark and Sherwood UnitedNewark and Sherwood United 0-0 Boston Town | Emirates FA Cup Preliminary Round |
| 8 | Sat 30 Aug | 91-1 v Sporting KhalsaBoston Town 1-1 Sporting Khalsa | Emirates FA Cup First Qualifying Round |
| 9 | Tue 2 Sep | 90-2 v Sporting KhalsaSporting Khalsa 2-0 Boston Town | Emirates FA Cup First Qualifying Round Replay |
| 10 | Sat 6 Sep | 92-0 v Hucknall TownBoston Town 2-0 Hucknall Town | Sports Ground Development UCL Cup |
| 11 | Tue 23 Sep | 171-1 v Deeping RangersDeeping Rangers 1-1 Boston Town | United Counties League Premier Division North |
| 12 | Sat 25 Oct | 160-2 v Gresley RoversGresley Rovers 2-0 Boston Town | United Counties League Premier Division North |
| 13 | Tue 4 Nov | 171-0 v Newark and Sherwood UnitedNewark and Sherwood United 0-1 Boston Town | United Counties League Premier Division North |
| 14 | Sat 8 Nov | 92-2 v Belper UnitedBelper United 2-2 Boston Town | United Counties League Premier Division North |
| 15 | Tue 11 Nov | 96-0 v Harrowby UnitedBoston Town 6-0 Harrowby United | United Counties League Premier Division North |
| 16 | Sat 22 Nov | 91-1 v Eastwood CommunityEastwood Community 1-1 Boston Town | United Counties League Premier Division North |
| 17 | Sat 29 Nov | 91-0 v Kimberley Miners WelfareBoston Town 1-0 Kimberley Miners Welfare | United Counties League Premier Division North |
| 18 | Sat 13 Dec | 92-0 v Deeping RangersBoston Town 2-0 Deeping Rangers | United Counties League Premier Division North |
| 19 | Sat 20 Dec | 90-0 v Grantham TownGrantham Town 0-0 Boston Town | United Counties League Premier Division North |
| 20 | Sat 17 Jan | 94-1 v Belper UnitedBoston Town 4-1 Belper United | United Counties League Premier Division North |
| 21 | Tue 20 Jan | 90-1 v Grantham TownBoston Town 0-1 Grantham Town | Lincolnshire Senior Trophy Semi Final |
| 22 | Sat 24 Jan | 93-2 v Ashby IvanhoeBoston Town 3-2 Ashby Ivanhoe | United Counties League Premier Division North |
| 23 | Sat 31 Jan | 91-2 v Sherwood CollierySherwood Colliery 2-1 Boston Town | United Counties League Premier Division North |
| 24 | Sat 7 Feb | 92-5 v Heanor TownHeanor Town 5-2 Boston Town | United Counties League Premier Division North |
| 25 | Sat 14 Feb | 91-3 v Gresley RoversBoston Town 1-3 Gresley Rovers | United Counties League Premier Division North |
| 26 | Sat 28 Feb | 94-0 v Sherwood CollieryBoston Town 4-0 Sherwood Colliery | United Counties League Premier Division North |
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