FA Cup 2008/09, Extra Preliminary Round |
 | 16.08.2008 | | Tring Athletic | – | Berkhamsted Town | | 5:3 |
| |
FA Cup 2007/08, Preliminary Round |
| 01.09.2007 | | Aveley | – | Berkhamsted Town | | 2:1 |
| |
FA Cup 2006/07, Preliminary Round |
| 02.09.2006 | | Berkhamsted Town | – | AFC Sudbury | | 2:6 |
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FA Cup 2005/06, Second Qualifying Round |
| 24.09.2005 | | Farnborough Town | – | Berkhamsted Town | | 3:0 |
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FA Cup 2004/05, First Qualifying Round |
| | | Aveley | – | Berkhamsted Town | | 2:1 |
| |
FA Cup 2003/04, First Qualifying Round |
| | | Berkhamsted Town | – | AFC Sudbury | | 0:9 |
| |
FA Cup 2002/03, Preliminary Round |
| | | Berkhamsted Town | – | Banbury United | | 1:4 * |
| |
FA Cup 2001/02, Third Qualifying Round |
| | | Burton Albion | – | Berkhamsted Town | | 2:1 (2:0) |
| |
FA Cup 2000/01, Second Qualifying Round |
| | | Uxbridge | – | Berkhamsted Town | | 3:2 |
| |
FA Cup 1997/98, First Qualifying Round |
| | | Deal Town | – | Berkhamsted Town | | 2:1 * |
| |
FA Cup 1996/97, Preliminary Round |
| | | Berkhamsted Town | – | Chesham United | | 2:3 |
| |
FA Cup 1995/96, Second Qualifying Round |
| | | Berkhamsted Town | – | Dagenham & Redbridge | | 1:2 |
| |
FA Cup 1994/95, Preliminary Round |
| | | Berkhamsted Town | – | Baldock Town | | 1:3 |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Cambridge City | – | Berkhamsted Town | | 4:1 |
| |
FA Cup 1992/93, Third Qualifying Round |
| | | Chesham United | – | Berkhamsted Town | | 3:0 |
| |
FA Cup 1991/92, Third Qualifying Round |
| | | Berkhamsted Town | – | Slough Town | | 1:4 |
| |
FA Cup 1990/91, Preliminary Round |
| | | Harwich & Parkeston | – | Berkhamsted Town | | 4:1 |
| |
FA Cup 1989/90, Second Qualifying Round |
| | | Gravesend & Northfleet | – | Berkhamsted Town | | 1:0 |
| |
FA Cup 1988/89, Preliminary Round |
| | | March Town United | – | Berkhamsted Town | | 4:2 * |
| |
FA Cup 1987/88, Third Qualifying Round |
| | | Berkhamsted Town | – | Barnet | | 0:3 |
| |
FA Cup 1986/87, Preliminary Round |
| | | Tiptree United | – | Berkhamsted Town | | 2:1 * |
| |
FA Cup 1985/86, Second Qualifying Round |
| | | Stamford | – | Berkhamsted Town | | 3:0 |
| |
FA Cup 1984/85, First Qualifying Round |
| | | Valley Sports Rugby | – | Berkhamsted Town | | 3:1 * |
| |
FA Cup 1983/84, Preliminary Round |
| | | Dorking Town | – | Berkhamsted Town | | 1:0 |
| |
FA Cup 1982/83, Preliminary Round |
| | | Dulwich Hamlet | – | Berkhamsted Town | | 6:0 * |
| |
FA Cup 1981/82, First Qualifying Round |
| | | Berkhamsted Town | – | Hampton | | 0:3 |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Berkhamsted Town | – | Finchley | | 1:2 |
| |
FA Cup 1979/80, First Qualifying Round |
| | | Berkhamsted Town | – | Bedford Town | | 1:4 |
| |
FA Cup 1978/79, First Qualifying Round |
| | | Uxbridge | – | Berkhamsted Town | | 2:1 |
| |
FA Cup 1977/78, First Qualifying Round |
| | | Berkhamsted Town | – | Gravesend & Northfleet | | 0:5 |
| |
FA Cup 1958/59, Second Qualifying Round |
| | | Enfield | – | Berkhamsted Town | | 6:0 |
| |
FA Cup 1957/58, Preliminary Round |
| | | Wembley | – | Berkhamsted Town | | 3:0 |
| |
FA Cup 1956/57, Preliminary Round |
| | | Uxbridge | – | Berkhamsted Town | | 3:2 |
| |
FA Cup 1955/56, Preliminary Round |
| | | Kingstonian | – | Berkhamsted Town | | 6:0 * |
| |
FA Cup 1954/55, Preliminary Round |
| | | Berkhamsted Town | – | Hendon | | 0:3 |
| |
FA Cup 1953/54, Preliminary Round |
| | | Hemel Hempstead | – | Berkhamsted Town | | 4:2 * |
| |
FA Cup 1952/53, Preliminary Round |
| | | Berkhamsted Town | – | Barnet | | 1:5 |
| |
FA Cup 1951/52, First Qualifying Round |
| | | Hayes | – | Berkhamsted Town | | 5:0 |
| |
FA Cup 1950/51, Preliminary Round |
| | | Bicester Town | – | Berkhamsted Town | | 2:1 * |
| |
FA Cup 1949/50, Extra Preliminary Round |
| | | Southall | – | Berkhamsted Town | | 1:0 |
| |
FA Cup 1948/49, First Qualifying Round |
| | | Berkhamsted Town | – | Banbury Spencer | | 1:2 |
| |
FA Cup 1947/48, First Qualifying Round |
| | | Berkhamsted Town | – | Harrow Town | | 3:4 |
| |
FA Cup 1946/47, Preliminary Round |
| | | Hoddesdon Town | – | Berkhamsted Town | | 4:3 |
| |
FA Cup 1945/46, Preliminary Round |
| | | Harrow Town | – | Berkhamsted Town | | 8:0 |
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