| 1 | Sat 5 Jul | 114-1 v March Town UnitedBoston Town 4-1 March Town United | Friendly |
| 2 | Tue 8 Jul | 112-1 v Louth TownLouth Town 1-2 Boston Town | Friendly |
| 3 | Tue 15 Jul | 112-2 v Boston UnitedBoston Town 2-2 Boston United | Friendly |
| 4 | Tue 12 Aug | 102-1 v Newark TownBoston Town 2-1 Newark Town | United Counties League Premier Division North |
| 5 | Sat 16 Aug | 100-0 v Newark and Sherwood UnitedNewark and Sherwood United 0-0 Boston Town | Emirates FA Cup Preliminary Round |
| 6 | Sat 13 Sep | 153-1 v Hucknall TownHucknall Town 1-3 Boston Town | United Counties League Premier Division North |
| 7 | Tue 16 Sep | 147-2 v Wisbech TownBoston Town 7-2 Wisbech Town | United Counties League Premier Division North |
| 8 | Sat 20 Sep | 107-0 v BlackstonesBoston Town 7-0 Blackstones | United Counties League Premier Division North |
| 9 | Sat 27 Sep | 103-1 v Melton TownBoston Town 3-1 Melton Town | United Counties League Premier Division North |
| 10 | Tue 30 Sep | 15 2-1 v Sherwood CollierySherwood Colliery 1-2 Boston Town | Sports Ground Development UCL Cup First Round |
| 11 | Sat 4 Oct | 105-0 v Harrowby UnitedHarrowby United 0-5 Boston Town | United Counties League Premier Division North |
| 12 | Sat 18 Oct | 103-4 v Clay Cross TownBoston Town 3-4 Clay Cross Town | United Counties League Premier Division North |
| 13 | Sat 25 Oct | 100-2 v Gresley RoversGresley Rovers 2-0 Boston Town | United Counties League Premier Division North |
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