| 1 | Tue 22 Jul | 190-3 v Scunthorpe UnitedSkegness Town 0-3 Scunthorpe United | Friendly |
| 2 | Sun 27 Jul | 173-5 v Newark TownSkegness Town 3-5 Newark Town | United Counties League Premier Division North |
| 3 | Wed 30 Jul | 14 2-1 v BlackstonesBlackstones 1-2 Skegness Town | United Counties League Premier Division North |
| 4 | Sat 2 Aug | 42-0 v Godmanchester RoversSkegness Town 2-0 Godmanchester Rovers | Emirates FA Cup Extra Preliminary Round |
| 5 | Sat 9 Aug | 42-3 v Gresley RoversGresley Rovers 3-2 Skegness Town | United Counties League Premier Division North |
| 6 | Wed 13 Aug | 44-2 v Harrowby UnitedSkegness Town 4-2 Harrowby United | United Counties League Premier Division North |
| 7 | Sat 16 Aug | 41-1 v Lincoln UnitedSkegness Town 1-1 Lincoln United | Emirates FA Cup Preliminary Round |
| 8 | Tue 19 Aug | 4 2-1 v Lincoln UnitedLincoln United 1-2 Skegness Town | Emirates FA Cup Preliminary Round Replay |
| 9 | Sat 23 Aug | 41-1 v Eastwood CommunitySkegness Town 1-1 Eastwood Community | United Counties League Premier Division North |
| 10 | Tue 26 Aug | 42-1 v Wisbech TownWisbech Town 1-2 Skegness Town | United Counties League Premier Division North |
| 11 | Sat 30 Aug | 40-5 v Redditch UnitedRedditch United 5-0 Skegness Town | Emirates FA Cup First Qualifying Round |
| 12 | Tue 2 Sep | 41-1 v Deeping RangersDeeping Rangers 1-1 Skegness Town | United Counties League Premier Division North |
| 13 | Sat 6 Sep | 172-3 v PinxtonSkegness Town 2-3 Pinxton | Sports Ground Development UCL Cup |
| 14 | Sat 13 Sep | 42-0 v Newark and Sherwood UnitedSkegness Town 2-0 Newark and Sherwood United | United Counties League Premier Division North |
| 15 | Wed 17 Sep | 42-2 v Grantham TownSkegness Town 2-2 Grantham Town | United Counties League Premier Division North |
| 16 | Sat 20 Sep | 4 1-2 v Oadby TownSkegness Town 1-2 Oadby Town | Isuzu FA Vase Second Qualifying Round |
| 17 | Sat 4 Oct | 41-2 v Deeping RangersSkegness Town 1-2 Deeping Rangers | United Counties League Premier Division North |
| 18 | Sat 11 Oct | 41-3 v Melton TownMelton Town 3-1 Skegness Town | United Counties League Premier Division North |
| 19 | Tue 14 Oct | 41-1 v Louth TownLouth Town 1-1 Skegness Town | Lincolnshire Senior Trophy First Round |
| 20 | Sat 18 Oct | 43-1 v BlackstonesSkegness Town 3-1 Blackstones | United Counties League Premier Division North |
| 21 | Wed 22 Oct | 42-0 v Wisbech TownSkegness Town 2-0 Wisbech Town | United Counties League Premier Division North |
| 22 | Sat 25 Oct | 4 2-4 v AFC MansfieldAFC Mansfield 4-2 Skegness Town | United Counties League Premier Division North |
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