| 1 | Sat 19 Jul | 94-4 v Coalville TownSkegness Town 4-4 Coalville Town | Friendly |
| 2 | Tue 22 Jul | 110-3 v Scunthorpe UnitedSkegness Town 0-3 Scunthorpe United | Friendly |
| 3 | Sun 27 Jul | 113-5 v Newark TownSkegness Town 3-5 Newark Town | United Counties League Premier Division North |
| 4 | Wed 30 Jul | 112-1 v BlackstonesBlackstones 1-2 Skegness Town | United Counties League Premier Division North |
| 5 | Sat 2 Aug | 172-0 v Godmanchester RoversSkegness Town 2-0 Godmanchester Rovers | Emirates FA Cup Extra Preliminary Round |
| 6 | Sat 9 Aug | 122-3 v Gresley RoversGresley Rovers 3-2 Skegness Town | United Counties League Premier Division North |
| 7 | Wed 13 Aug | 114-2 v Harrowby UnitedSkegness Town 4-2 Harrowby United | United Counties League Premier Division North |
| 8 | Sat 16 Aug | 111-1 v Lincoln UnitedSkegness Town 1-1 Lincoln United | Emirates FA Cup Preliminary Round |
| 9 | Tue 19 Aug | 112-1 v Lincoln UnitedLincoln United 1-2 Skegness Town | Emirates FA Cup Preliminary Round Replay |
| 10 | Sat 23 Aug | 151-1 v Eastwood CommunitySkegness Town 1-1 Eastwood Community | United Counties League Premier Division North |
| 11 | Tue 26 Aug | 102-1 v Wisbech TownWisbech Town 1-2 Skegness Town | United Counties League Premier Division North |
| 12 | Sat 30 Aug | 160-5 v Redditch UnitedRedditch United 5-0 Skegness Town | Emirates FA Cup First Qualifying Round |
| 13 | Tue 2 Sep | 141-1 v Deeping RangersDeeping Rangers 1-1 Skegness Town | United Counties League Premier Division North |
| 14 | Sat 6 Sep | 22-3 v PinxtonSkegness Town 2-3 Pinxton | Sports Ground Development UCL Cup |
| 15 | Sat 13 Sep | 172-0 v Newark and Sherwood UnitedSkegness Town 2-0 Newark and Sherwood United | United Counties League Premier Division North |
| 16 | Wed 17 Sep | 172-2 v Grantham TownSkegness Town 2-2 Grantham Town | United Counties League Premier Division North |
| 17 | Sat 20 Sep | 111-2 v Oadby TownSkegness Town 1-2 Oadby Town | Isuzu FA Vase Second Qualifying Round |
| 18 | Sat 4 Oct | 161-2 v Deeping RangersSkegness Town 1-2 Deeping Rangers | United Counties League Premier Division North |
| 19 | Sat 11 Oct | 151-3 v Melton TownMelton Town 3-1 Skegness Town | United Counties League Premier Division North |
| 20 | Tue 14 Oct | 151-1 v Louth TownLouth Town 1-1 Skegness Town | Lincolnshire Senior Trophy First Round |
| 21 | Sat 18 Oct | 93-1 v BlackstonesSkegness Town 3-1 Blackstones | United Counties League Premier Division North |
| 22 | Wed 22 Oct | 92-0 v Wisbech TownSkegness Town 2-0 Wisbech Town | United Counties League Premier Division North |
| 23 | Sat 25 Oct | 92-4 v AFC MansfieldAFC Mansfield 4-2 Skegness Town | United Counties League Premier Division North |
| 24 | Sat 1 Nov | 110-4 v Ashby IvanhoeAshby Ivanhoe 4-0 Skegness Town | United Counties League Premier Division North |
| 25 | Sat 8 Nov | 71-1 v Hucknall TownSkegness Town 1-1 Hucknall Town | United Counties League Premier Division North |
| 26 | Sat 22 Nov | 116-1 v Belper UnitedSkegness Town 6-1 Belper United | United Counties League Premier Division North |
| 27 | Sat 29 Nov | 113-1 v Heanor TownHeanor Town 1-3 Skegness Town | United Counties League Premier Division North |
| 28 | Sat 6 Dec | 110-2 v Newark and Sherwood UnitedNewark and Sherwood United 2-0 Skegness Town | United Counties League Premier Division North |
Football Web Pages