| 1 | Sat 6 Sep | 11-0 v Clipstone WelfareClipstone Welfare 0-1 Gresley Rovers | Sports Ground Development UCL Cup |
| 2 | Tue 30 Sep | 130-2 v Eastwood CommunityEastwood Community 2-0 Gresley Rovers | United Counties League Premier Division North |
| 3 | Sat 4 Oct | 12-1 v March Town UnitedMarch Town United 1-2 Gresley Rovers | Sports Ground Development UCL Cup First Round |
| 4 | Sat 11 Oct | 12-0 v Heanor TownHeanor Town 0-2 Gresley Rovers | United Counties League Premier Division North |
| 5 | Sat 18 Oct | 13-2 v Northampton Sileby RangersGresley Rovers 3-2 Northampton Sileby Rangers | Isuzu FA Vase First Round |
| 6 | Tue 21 Oct | 10-2 v Clay Cross TownClay Cross Town 2-0 Gresley Rovers | United Counties League Premier Division North |
| 7 | Sat 25 Oct | 12-0 v Boston TownGresley Rovers 2-0 Boston Town | United Counties League Premier Division North |
| 8 | Tue 28 Oct | 10-7 v Clay Cross TownGresley Rovers 0-7 Clay Cross Town | Sports Ground Development UCL Cup Second Round |
| 9 | Sat 1 Nov | 11-1 v Harrowby UnitedHarrowby United 1-1 Gresley Rovers | United Counties League Premier Division North |
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