| 1 | Tue 11 Aug | 160-1 v Milton Keynes IrishMilton Keynes Irish 1-0 Winslow United | Southern League - Central Division |
| 2 | Mon 31 Aug | 52-1 v HadleyHadley 1-2 Winslow United | Southern League - Central Division |
| 3 | Tue 15 Sep | 41-1 v StotfoldStotfold 1-1 Winslow United | Southern League - Central Division |
| 4 | Tue 29 Sep | 42-1 v Barton RoversWinslow United 2-1 Barton Rovers | Southern League - Central Division |
| 5 | Sat 3 Oct | 46-0 v London LionsWinslow United 6-0 London Lions | Southern League - Central Division |
| 6 | Sat 10 Oct | 42-1 v Welwyn Garden CityWelwyn Garden City 1-2 Winslow United | Southern League - Central Division |
| 7 | Sat 17 Oct | 43-1 v Flackwell HeathWinslow United 3-1 Flackwell Heath | Southern League - Central Division |
| 8 | Tue 20 Oct | 43-3 v MarlowWinslow United 3-3 Marlow | Southern League - Central Division |
| 9 | Sat 24 Oct | 33-0 v BiggleswadeBiggleswade 0-3 Winslow United | Southern League - Central Division |
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