| 1 | Tue 11 Aug | 4 0-1 v Milton Keynes IrishMilton Keynes Irish 1-0 Winslow United | Southern League - Central Division |
| 2 | Sat 15 Aug | 33-1 v Royston TownWinslow United 3-1 Royston Town | Southern League - Central Division |
| 3 | Mon 31 Aug | 152-1 v HadleyHadley 1-2 Winslow United | Southern League - Central Division |
| 4 | Sat 3 Oct | 36-0 v London LionsWinslow United 6-0 London Lions | Southern League - Central Division |
| 5 | Sat 10 Oct | 122-1 v Welwyn Garden CityWelwyn Garden City 1-2 Winslow United | Southern League - Central Division |
| 6 | Tue 13 Oct | 53-1 v Didcot TownDidcot Town 1-3 Winslow United | Southern League - Central Division |
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