| Season | Round | Opponents | Venue | Score |
| 1987-88 | 1st Round | Glossopians | Away | 1 – 1 |
| 1st Round Replay | Glossopians | Home | 2 – 2 | |
| *Glossop won 5-4 on penalties | ||||
| 2nd Round | Mickleover R.B.L. | Away | 0 – 0 | |
| 2nd Round Replay | Mickleover R.B.L. | Home | 4 – 2 | |
| 3rd Round | Borrowash Victoria | Away | 3 – 8 | |
| 1988-89 | 1st Round | Rolls Royce (Derby) | Away | 3 – 0 |
| 2nd Round | Heanor Town | Home | 0 – 2 | |
| 1989-90 | 1st Round | Long Eaton United | Away | 0 – 2 |
| 1990-91 | 1st Round | Alfreton Town | Home | 3 – 1 |
| 2nd Round | Mickleover R.B.L. | Home | 3 – 3 | |
| 2nd Round Replay | Mickleover R.B.L. | Away | 1 – 4 | |
| 1991-92 | 1st Round | Shirebrook Colliery | Away | 1 – 0 |
| 2nd Round | West Hallam | Away | 2 – 0 | |
| 3rd Round | Gresley Rovers | Away | 2 – 3 | |
| 1992-93 | 1st Round | Glapwell | Home | 4 – 2 |
| 2nd Round | Sandiacre Town | Away | 4 – 2 | |
| 3rd Round | Stanton (Ilkeston) | Home | 4 – 0 | |
| 4th Round | Alfreton Town | Away | 1 – 4 | |
| 1993-94 | 1st Round | Rolls Royce (Derby) | Away | 8 – 1 |
| 2nd Round | Shirebrook Town | Home | 1 – 1 | |
| 2nd Round Replay | Shirebrook Town | Away | 3 – 1 | |
| 3rd Round | Alfreton Town | Home | 0 – 2 | |
| 1994-95 | 3rd Round | Buxton | Away | 0 – 4 |
| 1995-96 | 3rd Round | Mickleover Sports | Away | 4 – 4 |
| 3rd, Replay | Mickleover Sports | Home | 3 – 1 | |
| 4th Round | Newhall United | Home | 6 – 1 | |
| Semi-Final | Gresley Rovers | Away | 0 – 3 | |
| 1996-97 | 3rd Round | Ilkeston Town | Away | 2 – 4 |
| 1997-98 | 3rd Round | Buxton | Home | 1 – 0 |
| 4th Round | Alfreton Town | Home | 3 – 0 | |
| Semi-Final | Matlock Town | Home | 0 – 0 | |
| Semi-Final Replay | Matlock Town | Away | 1 – 3 | |
| 1998-99 | 3rd Round | Matlock Town | Away | 1 – 3 |
| 1999-2000 | 3rd Round | Staveley MW | Away | 4 – 3 |
| 4th Round | Mickleover Sports | Home | 1 – 2 | |
| 2000-01 | 3rd Round | Stapenhill | Away | P – P |
| *Match awarded to Glossop | ||||
| 4th Round | Graham Street Prims | Away | 2 – 1 | |
| Semi-Final | Alfreton Town | Home | 4 – 0 | |
| Final, 1st Leg | Glapwell | Away | 3 – 3 | |
| Final, 2nd Leg | Glapwell | Home | 2 – 2 | |
| *Glossop won 4-2 on penalties | ||||
| 2001-02 | 3rd Round | Buxton | Away | 3 – 2 |
| 4th Round | Gresley Rovers | Home | 1 – 4 | |
| 2002-03 | 3rd Round | Blackwell MW | Home | 2 – 1 |
| 4th Round | Alfreton Town | Away | 0 – 3 | |
| 2003-04 | 3rd Round | Matlock Town | Home | 1 – 2 |
| 2004-05 | 2nd Round | Long Eaton United | Home | 7 – 1 |
| 3rd Round | Mickleover Sports | Away | 2 – 1 | |
| Semi-Final | Gresley Rovers | Away | 0 – 2 | |
| 2005-06 | 2nd Round | Alfreton Town | Home | 1 – 3 |
| 2006-07 | 2nd Round | Belper Town | Away | 1 – 2 |
| 2007-08 | 2nd Round | Staveley Miners Welfare | Home | 3 – 2 |
| 3rd Round | Buxton | Away | 0 – 3 | |
| 2008-09 | 2nd Round | New Mills | Home | 3 – 1 |
| 3rd Round | Graham Street Prims | Home | 6 – 1 | |
| 4th Round | Matlock Town | Home | 0 – 1 | |
| 2009-10 | 1st Round | Newhall United | Away | 8 – 3 |
| 2nd Round | Glapwell | Home | 0 – 2 | |
| 2010-11 | 2nd Round | Stapenhill | Home | 5 – 0 |
| 3rd Round | Gresley | Home | 3 – 0 | |
| 4th Round | Borrowash Victoria | Home | 1 – 2 | |
| 2011-12 | 2nd Round | Pinxton | Home | 0 – 1 |
