| 1 | Tue 22 Jul | 150-3 v Scunthorpe UnitedSkegness Town 0-3 Scunthorpe United | Friendly |
| 2 | Wed 30 Jul | 52-1 v BlackstonesBlackstones 1-2 Skegness Town | United Counties League Premier Division North |
| 3 | Sat 2 Aug | 52-0 v Godmanchester RoversSkegness Town 2-0 Godmanchester Rovers | Emirates FA Cup Extra Preliminary Round |
| 4 | Sat 9 Aug | 52-3 v Gresley RoversGresley Rovers 3-2 Skegness Town | United Counties League Premier Division North |
| 5 | Wed 13 Aug | 5 4-2 v Harrowby UnitedSkegness Town 4-2 Harrowby United | United Counties League Premier Division North |
| 6 | Sat 16 Aug | 51-1 v Lincoln UnitedSkegness Town 1-1 Lincoln United | Emirates FA Cup Preliminary Round |
| 7 | Sat 6 Sep | 52-3 v PinxtonSkegness Town 2-3 Pinxton | Sports Ground Development UCL Cup |
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