| 1 | Sat 4 Oct | 61-2 v Deeping RangersSkegness Town 1-2 Deeping Rangers | United Counties League Premier Division North |
| 2 | Sat 11 Oct | 31-3 v Melton TownMelton Town 3-1 Skegness Town | United Counties League Premier Division North |
| 3 | Tue 14 Oct | 21-1 v Louth TownLouth Town 1-1 Skegness Town | Lincolnshire Senior Trophy First Round |
| 4 | Sat 18 Oct | 33-1 v BlackstonesSkegness Town 3-1 Blackstones | United Counties League Premier Division North |
| 5 | Wed 22 Oct | 32-0 v Wisbech TownSkegness Town 2-0 Wisbech Town | United Counties League Premier Division North |
| 6 | Sat 25 Oct | 32-4 v AFC MansfieldAFC Mansfield 4-2 Skegness Town | United Counties League Premier Division North |
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