| 1 | Tue 13 Aug | 62-0 v Matlock TownMatlock Town 0-2 Whitby Town | Northern Premier League - Premier Division |
| 2 | Sat 17 Aug | 15 1-0 v Warrington RylandsWarrington Rylands 0-1 Whitby Town | Northern Premier League - Premier Division |
| 3 | Tue 20 Aug | 150-0 v FC United of ManchesterWhitby Town 0-0 FC United of Manchester | Northern Premier League - Premier Division |
| 4 | Sat 24 Aug | 162-3 v MacclesfieldWhitby Town 2-3 Macclesfield | Northern Premier League - Premier Division |
| 5 | Mon 26 Aug | 2 0-2 v Stockton TownStockton Town 2-0 Whitby Town | Northern Premier League - Premier Division |
| 6 | Sat 31 Aug | 22-2 v MossleyMossley 2-2 Whitby Town | Emirates FA Cup First Qualifying Round |
| 7 | Tue 3 Sep | 43-3 v MossleyWhitby Town 3-3 Mossley | Emirates FA Cup First Qualifying Round Replay |
| 8 | Sat 7 Sep | 41-5 v Ilkeston TownIlkeston Town 5-1 Whitby Town | Northern Premier League - Premier Division |
| 9 | Tue 10 Sep | 51-2 v GuiseleyWhitby Town 1-2 Guiseley | Northern Premier League - Premier Division |
| 10 | Sat 14 Sep | 21-2 v Ashton UnitedWhitby Town 1-2 Ashton United | Northern Premier League - Premier Division |
| 11 | Tue 17 Sep | 26-2 v Hebburn TownHebburn Town 2-6 Whitby Town | Northern Premier League - Premier Division |
| 12 | Sat 21 Sep | 21-3 v Workington AFCWorkington AFC 3-1 Whitby Town | Northern Premier League - Premier Division |
| 13 | Sat 28 Sep | 50-0 v Matlock TownWhitby Town 0-0 Matlock Town | Northern Premier League - Premier Division |
| 14 | Sat 5 Oct | 150-1 v Newton AycliffeWhitby Town 0-1 Newton Aycliffe | Isuzu FA Trophy Third Qualifying Round |
| 15 | Sat 2 Nov | 72-1 v Prescot CablesWhitby Town 2-1 Prescot Cables | Northern Premier League - Premier Division |
| 16 | Tue 5 Nov | 70-2 v Gainsborough TrinityWhitby Town 0-2 Gainsborough Trinity | Northern Premier League - Premier Division |
| 17 | Sat 9 Nov | 74-3 v Basford UnitedBasford United 3-4 Whitby Town | Northern Premier League - Premier Division |
| 18 | Tue 12 Nov | 70-3 v Worksop TownWorksop Town 3-0 Whitby Town | Northern Premier League - Premier Division |
| 19 | Sat 16 Nov | 74-1 v MickleoverWhitby Town 4-1 Mickleover | Northern Premier League - Premier Division |
| 20 | Wed 27 Nov | 120-1 v Great Ayton United RoyalsGreat Ayton United Royals 1-0 Whitby Town | North Riding Senior Cup Second Round |
| 21 | Sat 30 Nov | 7 3-0 v Lancaster CityWhitby Town 3-0 Lancaster City | Northern Premier League - Premier Division |
| 22 | Sat 7 Dec | 71-3 v GuiseleyGuiseley 3-1 Whitby Town | Northern Premier League - Premier Division |
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