| 1 | Sat 23 Aug | 52-5 v Hyde UnitedHyde United 5-2 Whitby Town | Northern Premier League - Premier Division |
| 2 | Sat 30 Aug | 5 2-1 v Lancaster CityLancaster City 1-2 Whitby Town | Emirates FA Cup First Qualifying Round |
| 3 | Sat 13 Sep | 40-2 v Hyde UnitedHyde United 2-0 Whitby Town | Emirates FA Cup Second Qualifying Round |
| 4 | Tue 14 Oct | 62-1 v Hednesford TownWhitby Town 2-1 Hednesford Town | Northern Premier League - Premier Division |
| 5 | Sat 13 Dec | 40-0 v Stockton TownStockton Town 0-0 Whitby Town | Northern Premier League - Premier Division |
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