FA Cup 2020/21, Preliminary Round |
 | 12.09.2020 |  | Stamford | – | Diss Town | | 4:0 |
| Stamford |
FA Cup 2017/18, Extra Preliminary Round |
| 05.08.2017 | | Great Yarmouth Town | – | Diss Town | | 5:0 |
| Great Yarmouth |
FA Cup 2015/16, Extra Preliminary Round |
| 15.08.2015 | | Wisbech Town | – | Diss Town | | 1:0 |
| Wisbech |
FA Cup 2014/15, Extra Preliminary Round |
| 16.08.2014 | | Diss Town | – | Holbeach United | | 1:5 |
| Diss |
FA Cup 2013/14, Extra Preliminary Round |
| 16.08.2013 | | Thetford Town | – | Diss Town | | 1:0 |
| Thetford |
FA Cup 2012/13, Extra Preliminary Round |
| 11.08.2012 | | Basildon United | – | Diss Town | | 1:0 |
| |
FA Cup 2011/12, Extra Preliminary Round |
| 20.08.2011 | | Ely City | – | Diss Town | | 4:0 |
| |
FA Cup 2010/11, Extra Preliminary Round |
| 14.08.2010 | | Diss Town | – | Daventry United | | 1:2 |
| |
FA Cup 2009/10, Extra Preliminary Round |
| 15.08.2009 | | Diss Town | – | Cogenhoe United | | 2:3 |
| |
FA Cup 2008/09, Extra Preliminary Round |
| 16.08.2008 | | Diss Town | – | Walsham Le Willows | | 1:2 |
| |
FA Cup 2007/08, Preliminary Round |
| 01.09.2007 | | Diss Town | – | Kirkley & Pakefield | | 0:1 |
| |
FA Cup 2006/07, Extra Preliminary Round |
| 19.08.2006 | | Tring Athletic | – | Diss Town | | 2:1 |
| |
FA Cup 2005/06, First Qualifying Round |
| 10.09.2005 | | Wroxham | – | Diss Town | | 2:0 |
| |
FA Cup 2004/05, Preliminary Round |
| | | Diss Town | – | Barking & East Ham United | | 0:2 |
| |
FA Cup 2003/04, Preliminary Round |
| | | AFC Sudbury | – | Diss Town | | 4:3 |
| |
FA Cup 2002/03, Second Qualifying Round |
| | | Diss Town | – | Chertsey Town | | 2:3 |
| |
FA Cup 2001/02, First Qualifying Round |
| | | Diss Town | – | Southend Manor | | 1:2 * |
| |
FA Cup 2000/01, First Qualifying Round |
| | | Diss Town | – | Bishop's Stortford | | 0:5 |
| |
FA Cup 1999/00, Preliminary Round |
| | | Diss Town | – | Sudbury Town | | 1:6 |
| |
FA Cup 1998/99, First Qualifying Round |
| | | Harlow Town | – | Diss Town | | 5:0 |
| |
FA Cup 1997/98, First Qualifying Round |
| | | Diss Town | – | Valley Sports Rugby | | 0:1 |
| |
FA Cup 1996/97, First Qualifying Round |
| | | Cambridge City | – | Diss Town | | 6:1 |
| |
FA Cup 1995/96, First Qualifying Round |
| | | Diss Town | – | Heybridge Swifts | | 0:2 |
| |
FA Cup 1994/95, Second Qualifying Round |
| | | Braintree Town | – | Diss Town | | 2:1 |
| |
FA Cup 1959/60, First Qualifying Round |
| | | Diss Town | – | Gorleston | | 1:2 * |
| |
FA Cup 1958/59, First Qualifying Round |
| | | Gorleston | – | Diss Town | | 3:2 |
| |
FA Cup 1957/58, Preliminary Round |
| | | Haverhill Rovers | – | Diss Town | | 6:1 |
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FA Cup 1956/57, Second Qualifying Round |
| | | Diss Town | – | Bury Town | | 2:4 |
| |
FA Cup 1955/56, First Qualifying Round |
| | | Stowmarket | – | Diss Town | | 7:0 |
| |
FA Cup 1954/55, First Qualifying Round |
| | | Diss Town | – | Stowmarket | | 1:3 |
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FA Cup 1953/54, First Qualifying Round |
| | | Sudbury Town | – | Diss Town | | 2:1 |
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FA Cup 1952/53, First Qualifying Round |
| | | Diss Town | – | Lowestoft Town | | 1:4 |
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FA Cup 1951/52, First Qualifying Round |
| | | Diss Town | – | Sudbury Town | | 0:4 |
| |
FA Cup 1950/51, Extra Preliminary Round |
| | | Beccles | – | Diss Town | | 4:2 |
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