| 1 | Sat 25 Jul | 12-3 v Hucknall TownHucknall Town 3-2 Skegness Town | United Counties League Premier Division North |
| 2 | Sat 1 Aug | 12-2 v Hinckley AFCSkegness Town 2-2 Hinckley AFC | United Counties League Premier Division North |
| 3 | Sat 8 Aug | 10-2 v Retford FCSkegness Town 0-2 Retford FC | Emirates FA Cup Extra Preliminary Round |
| 4 | Sat 19 Sep | 11-1 v Leicester NirvanaSkegness Town 1-1 Leicester Nirvana | United Counties League Premier Division North |
| 5 | Sat 26 Sep | 14-1 v West Bridgford ColtsWest Bridgford Colts 1-4 Skegness Town | Sports Ground Development UCL Cup First Round |
| 6 | Wed 30 Sep | 12-5 v BlackstonesBlackstones 5-2 Skegness Town | United Counties League Premier Division North |
| 7 | Sat 3 Oct | 10-0 v Ashby IvanhoeSkegness Town 0-0 Ashby Ivanhoe | United Counties League Premier Division North |
| 8 | Wed 14 Oct | 12-0 v Brigg TownSkegness Town 2-0 Brigg Town | Lincolnshire Senior Trophy First Round |
| 9 | Sat 17 Oct | 10-2 v Belper UnitedBelper United 2-0 Skegness Town | United Counties League Premier Division North |
| 10 | Sat 24 Oct | 13-2 v St Neots TownSt Neots Town 2-3 Skegness Town | Sports Ground Development UCL Cup Second Round |
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