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