| 1 | Sat 15 Aug | 53-1 v Royston TownWinslow United 3-1 Royston Town | Southern League - Central Division |
| 2 | Mon 31 Aug | 172-1 v HadleyHadley 1-2 Winslow United | Southern League - Central Division |
| 3 | Tue 15 Sep | 161-1 v StotfoldStotfold 1-1 Winslow United | Southern League - Central Division |
| 4 | Tue 29 Sep | 162-1 v Barton RoversWinslow United 2-1 Barton Rovers | Southern League - Central Division |
| 5 | Sat 10 Oct | 162-1 v Welwyn Garden CityWelwyn Garden City 1-2 Winslow United | Southern League - Central Division |
| 6 | Tue 13 Oct | 163-1 v Didcot TownDidcot Town 1-3 Winslow United | Southern League - Central Division |
| 7 | Sat 17 Oct | 163-1 v Flackwell HeathWinslow United 3-1 Flackwell Heath | Southern League - Central Division |
| 8 | Sat 24 Oct | 163-0 v BiggleswadeBiggleswade 0-3 Winslow United | Southern League - Central Division |
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