| 1 | Sat 25 Jul | 82-3 v Hucknall TownHucknall Town 3-2 Skegness Town | United Counties League Premier Division North |
| 2 | Wed 29 Jul | 82-1 v Deeping RangersSkegness Town 2-1 Deeping Rangers | United Counties League Premier Division North |
| 3 | Sat 1 Aug | 4 2-2 v Hinckley AFCSkegness Town 2-2 Hinckley AFC | United Counties League Premier Division North |
| 4 | Sat 8 Aug | 40-2 v Retford FCSkegness Town 0-2 Retford FC | Emirates FA Cup Extra Preliminary Round |
| 5 | Sat 15 Aug | 41-1 v Eastwood CFCSkegness Town 1-1 Eastwood CFC | FA Vase |
| 6 | Tue 18 Aug | 43-1 v AFC MansfieldAFC Mansfield 1-3 Skegness Town | United Counties League Premier Division North |
| 7 | Sat 22 Aug | 100-1 v Kimberley Miners WelfareSkegness Town 0-1 Kimberley Miners Welfare | United Counties League Premier Division North |
| 8 | Sat 29 Aug | 41-0 v Maltby MainMaltby Main 0-1 Skegness Town | Sports Ground Development UCL Cup Preliminary Round |
| 9 | Wed 2 Sep | 44-2 v BlackstonesSkegness Town 4-2 Blackstones | United Counties League Premier Division North |
| 10 | Sat 5 Sep | 101-1 v SheffieldSkegness Town 1-1 Sheffield | United Counties League Premier Division North |
| 11 | Sat 12 Sep | 10 1-3 v Gresley RoversGresley Rovers 3-1 Skegness Town | United Counties League Premier Division North |
| 12 | Sat 19 Sep | 41-1 v Leicester NirvanaSkegness Town 1-1 Leicester Nirvana | United Counties League Premier Division North |
| 13 | Sat 26 Sep | 44-1 v West Bridgford ColtsWest Bridgford Colts 1-4 Skegness Town | Sports Ground Development UCL Cup First Round |
| 14 | Wed 30 Sep | 42-5 v BlackstonesBlackstones 5-2 Skegness Town | United Counties League Premier Division North |
| 15 | Sat 3 Oct | 40-0 v Ashby IvanhoeSkegness Town 0-0 Ashby Ivanhoe | United Counties League Premier Division North |
| 16 | Wed 14 Oct | 42-0 v Brigg TownSkegness Town 2-0 Brigg Town | Lincolnshire Senior Trophy First Round |
| 17 | Sat 17 Oct | 40-2 v Belper UnitedBelper United 2-0 Skegness Town | United Counties League Premier Division North |
| 18 | Sat 24 Oct | 43-2 v St Neots TownSt Neots Town 2-3 Skegness Town | Sports Ground Development UCL Cup Second Round |
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