| Sat 26 Jul | Boston Town | 2 | Heanor | 2 | UCL | D | Munton, Tate |
| Tue 29 Jul | Wisbech Town | 2 | Boston Town | 1 | UCL | L | Nuttell |
| Sat 2 Aug | Boston Town | 2 | Kimberley MW | 0 | FA Cup | W | Bayliss, Ford |
| Sat 9 Aug | Ashby Ivanhoe | 1 | Boston Town | 2 | UCL | W | Munton, Limb (pen) |
| Tue 12 Aug | Boston Town | 2 | Newark Town | 1 | UCL | W | Cotton 2 |
| Sat 16 Aug | Newark & Sherwood | 0 | Boston Town | 0 | FA Cup | D | |
| Tue 19 Aug | Boston Town | 4 | Newark & Sherwood | 1 | FA Cup | W | Bayliss 2, Gurney, Zaluzinskis |
| Sat 23 Aug | Hucknall Town | 3 | Boston Town | 1 | FA Vase | L | Bayliss |
| Mon 25 Aug | Boston Town | 3 | AFC Mansfield | 1 | UCL | W | Cotton 2 (1 pen), Maddison |
| Sat 30 Aug | Boston Town | 1 | Sporting Khalsa | 1 | FA Cup | D | Cotton |
| Tue 2 Sep | Sporting Khalsa | 2 | Boston Town | 0 | FA Cup | L | |
| Sat 6 Sep | Boston Town | 2 | Hucknall Town | 0 | KO Cup | W | Bayliss 2 |
| Sat 13 Sep | Hucknall Town | 1 | Boston Town | 3 | UCL | W | Tate, Bayliss, Cotton |
| Tue 16 Sep | Boston Town | 7 | Wisbech Town | 2 | UCL | W | Bayliss 3, Gurney 2, Cotton, Limb |
| Sat 20 Sep | Boston Town | 7 | Blackstones | 0 | UCL | W | Limb 2 (1 pen), Cotton 2, Gurney, Smith, Tate |
| Tue 23 Sep | Deeping Rangers | 1 | Boston Town | 1 | UCL | D | Cotton |
| Sat 27 Sep | Boston Town | 3 | Melton Town | 1 | UCL | W | Cotton 2, Ford |
| Tue 30 Sep | Sherwood Colliery | 1 | Boston Town | 2 | KO Cup | W | Bayliss, Ford |
| Sat 4 Oct | Harrowby Utd | 0 | Boston Town | 5 | UCL | W | Limb 3 (1 pen), Cotton, Gurney |
| Sat 11 Oct | Boston Town | 3 | Bottesford | 1 | Lincs | W | Burdass, Bayliss, Limb |
| Wed 15 Oct | Blackstones | 1 | Boston Town | 2 | UCL | W | Wilson, Cotton |
| Sat 18 Oct | Boston Town | 3 | Clay Cross | 4 | UCL | L | Tate, Bayliss, Cotton (pen) |
| Tue 21 Oct | Boston Town | 0 | Grantham | 1 | UCL | L | |
| Sat 25 Oct | Gresley Rovers | 2 | Boston Town | 0 | UCL | L | |
| Sat 1 Nov | Moulton | 3 | Boston Town | 3 | KO Cup | D | Cotton 3 (1 pen) [lost 4-3 on pens] |
| Tue 4 Nov | Newark & Sherwood | 0 | Boston Town | 1 | UCL | W | Cotton |
| Sat 8 Nov | Belper United | 2 | Boston Town | 2 | UCL | D | Munton, Cotton |
| Tue 11 Nov | Boston Town | 6 | Harrowby | 0 | UCL | W | Cotton 4, Munton 2 |
| Wed 19 Nov | Blackstones | 0 | Boston Town | 4 | Lincs | W | Munton 2, Burdass, Tate |
| Sat 22 Nov | Eastwood CFC | 1 | Boston Town | 1 | UCL | D | Maddison |
| Sat 29 Nov | Boston Town | 1 | Kimberley MW | 0 | UCL | W | Cotton |
| Sat 6 Dec | AFC Mansfield | 0 | Boston Town | 1 | UCL | W | Cotton |
| Sat 13 Dec | Boston Town | 2 | Deeping Rangers | 0 | UCL | W | Munton, Wilson |