| 1 | Sat 16 Aug | 91-1 v Lincoln UnitedSkegness Town 1-1 Lincoln United | Emirates FA Cup Preliminary Round |
| 2 | Tue 19 Aug | 142-1 v Lincoln UnitedLincoln United 1-2 Skegness Town | Emirates FA Cup Preliminary Round Replay |
| 3 | Sat 23 Aug | 171-1 v Eastwood CommunitySkegness Town 1-1 Eastwood Community | United Counties League Premier Division North |
| 4 | Tue 26 Aug | 142-1 v Wisbech TownWisbech Town 1-2 Skegness Town | United Counties League Premier Division North |
| 5 | Sat 30 Aug | 140-5 v Redditch UnitedRedditch United 5-0 Skegness Town | Emirates FA Cup First Qualifying Round |
| 6 | Tue 2 Sep | 111-1 v Deeping RangersDeeping Rangers 1-1 Skegness Town | United Counties League Premier Division North |
| 7 | Sat 6 Sep | 122-3 v PinxtonSkegness Town 2-3 Pinxton | Sports Ground Development UCL Cup |
| 8 | Sat 13 Sep | 122-0 v Newark and Sherwood UnitedSkegness Town 2-0 Newark and Sherwood United | United Counties League Premier Division North |
| 9 | Sat 20 Sep | 121-2 v Oadby TownSkegness Town 1-2 Oadby Town | Isuzu FA Vase Second Qualifying Round |
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