| 1 | Sat 16 Sep | 2 2-1 v Prescot CablesWhitby Town 2-1 Prescot Cables | Emirates FA Cup Second Qualifying Round |
| 2 | Sat 23 Sep | 21-1 v FC United of ManchesterFC United of Manchester 1-1 Whitby Town | Northern Premier League - Premier Division |
| 3 | Sat 30 Sep | 21-0 v Morpeth TownWhitby Town 1-0 Morpeth Town | Emirates FA Cup Third Qualifying Round |
| 4 | Sat 7 Oct | 22-3 v RadcliffeRadcliffe 3-2 Whitby Town | Isuzu FA Trophy Third Qualifying Round |
| 5 | Sat 14 Oct | 22-2 v Chelmsford CityChelmsford City 2-2 Whitby Town | Emirates FA Cup Fourth Qualifying Round |
| 6 | Tue 17 Oct | 23-1 v Chelmsford CityWhitby Town 3-1 Chelmsford City | Emirates FA Cup Fourth Qualifying Round Replay |
| 7 | Mon 23 Oct | 21-1 v Bradford (Park Avenue)Bradford (Park Avenue) 1-1 Whitby Town | Northern Premier League - Premier Division |
| 8 | Sat 4 Nov | 22-7 v Bristol RoversBristol Rovers 7-2 Whitby Town | Emirates FA Cup First Round |
| 9 | Tue 7 Nov | 22-1 v Hyde UnitedHyde United 1-2 Whitby Town | Northern Premier League - Premier Division |
| 10 | Sat 11 Nov | 21-2 v MacclesfieldMacclesfield 2-1 Whitby Town | Northern Premier League - Premier Division |
| 11 | Tue 21 Nov | 151-0 v RadcliffeRadcliffe 0-1 Whitby Town | Northern Premier League - Premier Division |
| 12 | Sat 25 Nov | 171-1 v Workington AFCWhitby Town 1-1 Workington AFC | Northern Premier League - Premier Division |
| 13 | Tue 28 Nov | 21-2 v Lancaster CityLancaster City 2-1 Whitby Town | Northern Premier League - Premier Division |
| 14 | Sat 2 Dec | 21-1 v Basford UnitedBasford United 1-1 Whitby Town | Northern Premier League - Premier Division |
| 15 | Sat 23 Dec | 21-1 v MarineWhitby Town 1-1 Marine | Northern Premier League - Premier Division |
| 16 | Tue 26 Dec | 171-0 v Morpeth TownMorpeth Town 0-1 Whitby Town | Northern Premier League - Premier Division |
| 17 | Mon 1 Jan | 123-0 v Ilkeston TownWhitby Town 3-0 Ilkeston Town | Northern Premier League - Premier Division |
| 18 | Sat 6 Jan | 20-1 v Worksop TownWorksop Town 1-0 Whitby Town | Northern Premier League - Premier Division |
| 19 | Tue 6 Feb | 23-1 v Northallerton TownNorthallerton Town 1-3 Whitby Town | North Riding Senior Cup Second Round |
| 20 | Tue 5 Mar | 2 1-0 v Matlock TownWhitby Town 1-0 Matlock Town | Northern Premier League - Premier Division |
| 21 | Sat 9 Mar | 20-1 v Gainsborough TrinityWhitby Town 0-1 Gainsborough Trinity | Northern Premier League - Premier Division |
| 22 | Tue 12 Mar | 21-1 v Guisborough TownGuisborough Town 1-1 Whitby Town | North Riding Senior Cup Semi Final |
| 23 | Tue 19 Mar | 2 1-2 v GuiseleyWhitby Town 1-2 Guiseley | Northern Premier League - Premier Division |
| 24 | Sat 23 Mar | 25-1 v Matlock TownMatlock Town 1-5 Whitby Town | Northern Premier League - Premier Division |
| 25 | Tue 26 Mar | 2 1-2 v FC United of ManchesterWhitby Town 1-2 FC United of Manchester | Northern Premier League - Premier Division |
| 26 | Fri 29 Mar | 2 1-4 v Ashton UnitedAshton United 4-1 Whitby Town | Northern Premier League - Premier Division |
| 27 | Sat 6 Apr | 20-1 v Stafford RangersStafford Rangers 1-0 Whitby Town | Northern Premier League - Premier Division |
| 28 | Sat 13 Apr | 21-2 v RadcliffeWhitby Town 1-2 Radcliffe | Northern Premier League - Premier Division |
| 29 | Tue 16 Apr | 23-1 v Morpeth TownWhitby Town 3-1 Morpeth Town | Northern Premier League - Premier Division |
| 30 | Sat 20 Apr | 22-3 v Bamber BridgeBamber Bridge 3-2 Whitby Town | Northern Premier League - Premier Division |
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