Season	Round	Opponents	Venue	Score
1992-93	1st Round	Flixton	Away	4 – 1
	2nd Round	Hyde United	Away	0 – 4
1993-94	2nd Round	Ashton United	Home	1 – 4
1994-95	1st Round	Mossley	Away	2 – 1
	2nd Round	Hyde United	Away	0 – 1
1995-96	1st Round	Radcliffe Borough	Away	1 – 2
1996-97	1st Round	Maine Road	Home	3 – 0
	2nd Round	Radcliffe Borough	Away	3 – 1
	Semi-Final	Ashton United	Away	3 – 3
		*Glossop won 5-4 on penalties
	Final	Trafford	MUFC	1 – 1
		*Glossop won 5-4 on penalties
1997-98	1st Round	Maine Road	Home	3 – 0
	2nd Round	Salford City	Home	8 – 0
	Semi-Final	Flixton	Home	2 – 1
	Final	Radcliffe Borough	MCFC	1 – 0
1998-99	1st Round	Trafford	Home	2 – 0
	2nd Round	Woodley Sports	Home	2 – 0
	Semi-Final	Hyde United	Home	1 – 3
1999-2003	*Glossop were not invited to enter
2004-05	1st Round	Hyde United	Away	0 – 2
2005-06	1st Round	Maine Road	Home	0 – 2
2006-07	1st Round	Trafford	Home	1 – 0
	2nd Round	Oldham Town	Home	1 – 3
2007-08	1st Round	Hyde United	Away	4 – 6
2008-09	1st Round	Curzon Ashton	Home	1 – 2
2009-10	1st Round	Abbey Hey	Away	2 – 2
		*Glossop won 5-4 on penalties
	2nd Round	Mossley	Home	2 – 1
	Semi-Final	Droylsden	Away	0 – 2
2010-11	1st Round	Radcliffe Borough	Home	3 – 1
	2nd Round	Trafford	Away	1 – 3
2011-12	1st Round	New Mills	Home	2 – 3