| 1 | Tue 11 Aug | 180-1 v Milton Keynes IrishMilton Keynes Irish 1-0 Winslow United | Southern League - Central Division |
| 2 | Sat 15 Aug | 193-1 v Royston TownWinslow United 3-1 Royston Town | Southern League - Central Division |
| 3 | Tue 15 Sep | 61-1 v StotfoldStotfold 1-1 Winslow United | Southern League - Central Division |
| 4 | Tue 29 Sep | 212-1 v Barton RoversWinslow United 2-1 Barton Rovers | Southern League - Central Division |
| 5 | Sat 3 Oct | 206-0 v London LionsWinslow United 6-0 London Lions | Southern League - Central Division |
| 6 | Sat 10 Oct | 202-1 v Welwyn Garden CityWelwyn Garden City 1-2 Winslow United | Southern League - Central Division |
| 7 | Tue 13 Oct | 203-1 v Didcot TownDidcot Town 1-3 Winslow United | Southern League - Central Division |
| 8 | Sat 17 Oct | 183-1 v Flackwell HeathWinslow United 3-1 Flackwell Heath | Southern League - Central Division |
| 9 | Tue 20 Oct | 183-3 v MarlowWinslow United 3-3 Marlow | Southern League - Central Division |
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