| 1 | Sat 25 Oct | 10-2 v Gresley RoversGresley Rovers 2-0 Boston Town | United Counties League Premier Division North |
| 2 | Sat 1 Nov | 13-3 v MoultonMoulton 3-3 Boston Town | Sports Ground Development UCL Cup Second Round |
| 3 | Tue 4 Nov | 11-0 v Newark and Sherwood UnitedNewark and Sherwood United 0-1 Boston Town | United Counties League Premier Division North |
| 4 | Sat 8 Nov | 12-2 v Belper UnitedBelper United 2-2 Boston Town | United Counties League Premier Division North |
| 5 | Tue 11 Nov | 16-0 v Harrowby UnitedBoston Town 6-0 Harrowby United | United Counties League Premier Division North |
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