Head to Head
| England Northern League Challenge Cup | 2015/10/06 18:45 | Workington v Whitby | L | 3-1 |
| England Northern League Challenge Cup | 2015/01/03 15:00 | Workington v Whitby | L | 3-0 |
| England Northern League Challenge Cup | 2014/10/08 18:45 | Whitby v Workington | D | 0-0 |
Home History
| England Northern League Challenge Cup | 2016/01/30 15:00 | Whitby v Halesowen | W | 2-1 |
| England Northern League Challenge Cup | 2016/01/23 15:00 | Stamford v Whitby | D | 2-2 |
| England Northern League Challenge Cup | 2016/01/19 19:45 | Darlington 1883 v Whitby | D | 2-2 |
| England Northern League Challenge Cup | 2016/01/02 15:00 | Nantwich Town v Whitby | W | 1-2 |
| England Northern League Challenge Cup | 2015/12/28 15:00 | Whitby v Frickley | D | 1-1 |
| England Northern League Challenge Cup | 2015/12/19 15:00 | Whitby v Sutton Coldfield | L | 0-1 |
| England Northern League Challenge Cup | 2015/11/28 15:00 | Whitby v Mickleover Sports | W | 4-1 |
| England Northern League Challenge Cup | 2015/11/21 15:00 | Mickleover Sports v Whitby | L | 1-0 |
Away History
| England Northern League Challenge Cup | 2016/02/06 15:00 | Workington v Marine | W | 1-0 |
| England Northern League Challenge Cup | 2016/02/02 19:45 | Workington v Blyth Spartans | W | 2-0 |
| England Northern League Challenge Cup | 2016/01/25 19:45 | Hyde Utd v Workington | W | 0-4 |
| England Northern League Challenge Cup | 2016/01/23 15:00 | Workington v Halesowen | W | 3-0 |
| England Northern League Challenge Cup | 2016/01/16 15:00 | Grantham v Workington | W | 0-1 |
| England Northern League Challenge Cup | 2016/01/09 15:00 | Workington v Ashton Utd | W | 5-2 |
| England Northern League Challenge Cup | 2016/01/02 15:00 | Workington v Colwyn Bay | L | 1-2 |
| England Northern League Challenge Cup | 2015/12/19 15:00 | Barwell v Workington | W | 0-1 |