| 1 | Sat 15 Aug | 11-1 v Eastwood CFCSkegness Town 1-1 Eastwood CFC | FA Vase |
| 2 | Tue 18 Aug | 13-1 v AFC MansfieldAFC Mansfield 1-3 Skegness Town | United Counties League Premier Division North |
| 3 | Sat 22 Aug | 10-1 v Kimberley Miners WelfareSkegness Town 0-1 Kimberley Miners Welfare | United Counties League Premier Division North |
| 4 | Sat 29 Aug | 11-0 v Maltby MainMaltby Main 0-1 Skegness Town | Sports Ground Development UCL Cup Preliminary Round |
| 5 | Wed 2 Sep | 14-2 v BlackstonesSkegness Town 4-2 Blackstones | United Counties League Premier Division North |
| 6 | Sat 5 Sep | 11-1 v SheffieldSkegness Town 1-1 Sheffield | United Counties League Premier Division North |
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