| 1 | Sun 27 Jul | 16 3-5 v Newark TownSkegness Town 3-5 Newark Town | United Counties League Premier Division North | 1 |
| 2 | Wed 30 Jul | 16 2-1 v BlackstonesBlackstones 1-2 Skegness Town | United Counties League Premier Division North | 2 |
| 3 | Wed 13 Aug | 164-2 v Harrowby UnitedSkegness Town 4-2 Harrowby United | United Counties League Premier Division North | 1 |
| 4 | Tue 19 Aug | 92-1 v Lincoln UnitedLincoln United 1-2 Skegness Town | Emirates FA Cup Preliminary Round Replay | 1 |
| 5 | Sat 18 Oct | 15 3-1 v BlackstonesSkegness Town 3-1 Blackstones | United Counties League Premier Division North | 1 |
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