| 1 | Wed 27 Nov | 70-1 v Great Ayton United RoyalsGreat Ayton United Royals 1-0 Whitby Town | North Riding Senior Cup Second Round |
| 2 | Sat 30 Nov | 103-0 v Lancaster CityWhitby Town 3-0 Lancaster City | Northern Premier League - Premier Division |
| 3 | Sat 7 Dec | 101-3 v GuiseleyGuiseley 3-1 Whitby Town | Northern Premier League - Premier Division |
| 4 | Sat 14 Dec | 100-0 v Ilkeston TownWhitby Town 0-0 Ilkeston Town | Northern Premier League - Premier Division |
| 5 | Thu 26 Dec | 104-3 v Blyth SpartansBlyth Spartans 3-4 Whitby Town | Northern Premier League - Premier Division |
| 6 | Wed 1 Jan | 100-2 v Stockton TownWhitby Town 0-2 Stockton Town | Northern Premier League - Premier Division |
| 7 | Sat 4 Jan | 102-0 v Bamber BridgeBamber Bridge 0-2 Whitby Town | Northern Premier League - Premier Division |
| 8 | Sat 18 Jan | 100-5 v Ashton UnitedAshton United 5-0 Whitby Town | Northern Premier League - Premier Division |
| 9 | Sat 25 Jan | 101-3 v Workington AFCWhitby Town 1-3 Workington AFC | Northern Premier League - Premier Division |
| 10 | Sat 8 Feb | 100-2 v Morpeth TownWhitby Town 0-2 Morpeth Town | Northern Premier League - Premier Division |
| 11 | Sat 15 Feb | 10 2-1 v Leek TownLeek Town 1-2 Whitby Town | Northern Premier League - Premier Division |
| 12 | Tue 18 Feb | 101-1 v Hebburn TownWhitby Town 1-1 Hebburn Town | Northern Premier League - Premier Division |
| 13 | Sat 22 Feb | 100-1 v Prescot CablesPrescot Cables 1-0 Whitby Town | Northern Premier League - Premier Division |
| 14 | Sat 1 Mar | 101-3 v Worksop TownWhitby Town 1-3 Worksop Town | Northern Premier League - Premier Division |
| 15 | Sat 8 Mar | 10 1-1 v Hyde UnitedHyde United 1-1 Whitby Town | Northern Premier League - Premier Division |
| 16 | Sat 15 Mar | 101-0 v Basford UnitedWhitby Town 1-0 Basford United | Northern Premier League - Premier Division |
| 17 | Sat 22 Mar | 103-4 v MickleoverMickleover 4-3 Whitby Town | Northern Premier League - Premier Division |
| 18 | Tue 25 Mar | 101-2 v Gainsborough TrinityGainsborough Trinity 2-1 Whitby Town | Northern Premier League - Premier Division |
| 19 | Sat 29 Mar | 101-2 v Hyde UnitedWhitby Town 1-2 Hyde United | Northern Premier League - Premier Division |
| 20 | Sat 5 Apr | 91-0 v Lancaster CityLancaster City 0-1 Whitby Town | Northern Premier League - Premier Division |
| 21 | Sat 12 Apr | 10 1-0 v Warrington RylandsWhitby Town 1-0 Warrington Rylands | Northern Premier League - Premier Division |
| 22 | Fri 18 Apr | 10 3-2 v FC United of ManchesterFC United of Manchester 2-3 Whitby Town | Northern Premier League - Premier Division |
| 23 | Mon 21 Apr | 101-0 v Blyth SpartansWhitby Town 1-0 Blyth Spartans | Northern Premier League - Premier Division |
| 24 | Sat 26 Apr | 90-4 v MacclesfieldMacclesfield 4-0 Whitby Town | Northern Premier League - Premier Division |
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