| 1 | Sat 29 Aug | 171-0 v Maltby MainMaltby Main 0-1 Skegness Town | Sports Ground Development UCL Cup Preliminary Round |
| 2 | Sat 5 Sep | 141-1 v SheffieldSkegness Town 1-1 Sheffield | United Counties League Premier Division North |
| 3 | Sat 12 Sep | 2 1-3 v Gresley RoversGresley Rovers 3-1 Skegness Town | United Counties League Premier Division North |
| 4 | Sat 19 Sep | 101-1 v Leicester NirvanaSkegness Town 1-1 Leicester Nirvana | United Counties League Premier Division North |
| 5 | Sat 26 Sep | 84-1 v West Bridgford ColtsWest Bridgford Colts 1-4 Skegness Town | Sports Ground Development UCL Cup First Round |
| 6 | Wed 30 Sep | 152-5 v BlackstonesBlackstones 5-2 Skegness Town | United Counties League Premier Division North |
| 7 | Sat 24 Oct | 33-2 v St Neots TownSt Neots Town 2-3 Skegness Town | Sports Ground Development UCL Cup Second Round |
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