| 1 | Sun 27 Jul | 83-5 v Newark TownSkegness Town 3-5 Newark Town | United Counties League Premier Division North |
| 2 | Wed 30 Jul | 10 2-1 v BlackstonesBlackstones 1-2 Skegness Town | United Counties League Premier Division North |
| 3 | Sat 2 Aug | 112-0 v Godmanchester RoversSkegness Town 2-0 Godmanchester Rovers | Emirates FA Cup Extra Preliminary Round |
| 4 | Sat 9 Aug | 112-3 v Gresley RoversGresley Rovers 3-2 Skegness Town | United Counties League Premier Division North |
| 5 | Wed 13 Aug | 104-2 v Harrowby UnitedSkegness Town 4-2 Harrowby United | United Counties League Premier Division North |
| 6 | Sat 16 Aug | 10 1-1 v Lincoln UnitedSkegness Town 1-1 Lincoln United | Emirates FA Cup Preliminary Round |
| 7 | Tue 19 Aug | 82-1 v Lincoln UnitedLincoln United 1-2 Skegness Town | Emirates FA Cup Preliminary Round Replay |
| 8 | Sat 23 Aug | 81-1 v Eastwood CommunitySkegness Town 1-1 Eastwood Community | United Counties League Premier Division North |
| 9 | Tue 26 Aug | 82-1 v Wisbech TownWisbech Town 1-2 Skegness Town | United Counties League Premier Division North |
| 10 | Sat 30 Aug | 80-5 v Redditch UnitedRedditch United 5-0 Skegness Town | Emirates FA Cup First Qualifying Round |
| 11 | Tue 2 Sep | 81-1 v Deeping RangersDeeping Rangers 1-1 Skegness Town | United Counties League Premier Division North |
| 12 | Sat 6 Sep | 82-3 v PinxtonSkegness Town 2-3 Pinxton | Sports Ground Development UCL Cup |
| 13 | Sat 13 Sep | 112-0 v Newark and Sherwood UnitedSkegness Town 2-0 Newark and Sherwood United | United Counties League Premier Division North |
| 14 | Wed 17 Sep | 112-2 v Grantham TownSkegness Town 2-2 Grantham Town | United Counties League Premier Division North |
| 15 | Sat 20 Sep | 81-2 v Oadby TownSkegness Town 1-2 Oadby Town | Isuzu FA Vase Second Qualifying Round |
| 16 | Sat 4 Oct | 111-2 v Deeping RangersSkegness Town 1-2 Deeping Rangers | United Counties League Premier Division North |
| 17 | Sat 18 Oct | 163-1 v BlackstonesSkegness Town 3-1 Blackstones | United Counties League Premier Division North |
| 18 | Wed 22 Oct | 8 2-0 v Wisbech TownSkegness Town 2-0 Wisbech Town | United Counties League Premier Division North |
| 19 | Sat 25 Oct | 82-4 v AFC MansfieldAFC Mansfield 4-2 Skegness Town | United Counties League Premier Division North |
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