FA Cup 2023/24, Second Qualifying Round |
 | 16.09.2023 |  | Chippenham Town | – | Hungerford Town | | 1:4 (0:1) |
| Chippenham |
FA Cup 2022/23, Second Round Proper |
| 27.11.2022 | | Burton Albion | – | Chippenham Town | | 6:1 (2:0) |
| Burton upon Trent |
FA Cup 2021/22, Third qualifying round |
| 02.10.2021 | | Chippenham Town | – | Hastings United | | 0:1 (0:0) |
| Chippenham |
FA Cup 2020/21, Fourth Qualifying Round |
| 24.10.2020 | | Concord Rangers | – | Chippenham Town | | 2:1 |
| Canvey Island |
FA Cup 2019/20, First Round Proper |
| 10.11.2019 | | Chippenham Town | – | Northampton Town | | 0:3 (0:3) |
| Chippenham |
FA Cup 2018/19, Fourth Qualifying Round |
| 23.10.2018 | | Maidenhead United | – | Chippenham Town | | 1:0 (0:0) * |
| Maidenhead |
FA Cup 2017/18, Second Qualifying Round |
| 16.09.2017 | | Weymouth | – | Chippenham Town | | 2:0 (1:0) |
| Weymouth |
FA Cup 2016/17, Third Qualifying Round |
| 01.10.2016 | | Billericay Town | – | Chippenham Town | | 3:2 |
| Billericay |
FA Cup 2015/16, Fourth Qualifying Round |
| 24.10.2015 | | Chippenham Town | – | Maidstone United | | 0:2 (0:1) |
| Chippenham |
FA Cup 2014/15, Third Qualifying Round |
| 11.10.2014 | | Chippenham Town | – | Hemel Hempstead Town | | 0:5 (0:2) |
| Chippenham |
FA Cup 2013/14, First Qualifying Round |
| 14.09.2013 | | Yate Town | – | Chippenham Town | | 3:2 |
| Yate |
FA Cup 2012/13, Fourth Qualifying Round |
| 20.10.2012 | | Gloucester City | – | Chippenham Town | | 1:0 (0:0) |
| Cheltenham |
FA Cup 2010/11, Second Qualifying Round |
| 25.09.2010 | | Chippenham Town | – | Farnborough | | 0:1 |
| |
FA Cup 2009/10, Fourth Qualifying Round |
| 24.10.2009 | | Paulton Rovers | – | Chippenham Town | | 3:0 |
| |
FA Cup 2008/09, Third Qualifying Round |
| 11.10.2008 | | Ashford Town Middlesex | – | Chippenham Town | | 1:0 |
| |
FA Cup 2007/08, Fourth Qualifying Round |
| 27.10.2007 | | Chippenham Town | – | Horsham | | 2:3 (0:0) |
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FA Cup 2006/07, Second Qualifying Round |
| 30.09.2006 | | Slimbridge | – | Chippenham Town | | 3:1 |
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FA Cup 2005/06, First Round Proper |
| 14.11.2005 | | Worcester City | – | Chippenham Town | | 1:0 (0:0) * |
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FA Cup 2004/05, Second Qualifying Round |
| | | Lymington & New Milton | – | Chippenham Town | | 3:2 |
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FA Cup 2003/04, Third Qualifying Round |
| | | Gloucester City | – | Chippenham Town | | 4:3 (1:2) |
| |
FA Cup 2002/03, Second Qualifying Round |
| | | Chippenham Town | – | Weymouth | | 1:4 |
| |
FA Cup 2001/02, Second Qualifying Round |
| | | St Blazey | – | Chippenham Town | | 3:1 |
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FA Cup 2000/01, Second Qualifying Round |
| | | Chippenham Town | – | Gloucester City | | 3:5 * |
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FA Cup 1999/00, Third Qualifying Round |
| | | Worthing | – | Chippenham Town | | 3:1 * |
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FA Cup 1998/99, Preliminary Round |
| | | Cirencester Town | – | Chippenham Town | | 3:2 |
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FA Cup 1997/98, Third Qualifying Round |
| | | Yeovil Town | – | Chippenham Town | | 4:0 |
| |
FA Cup 1996/97, Preliminary Round |
| | | Mangotsfield United | – | Chippenham Town | | 6:1 |
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FA Cup 1995/96, Preliminary Round |
| | | Chippenham Town | – | Paulton Rovers | | 0:2 * |
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FA Cup 1994/95, Preliminary Round |
| | | Elmore | – | Chippenham Town | | 4:0 |
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FA Cup 1993/94, First Qualifying Round |
| | | Chippenham Town | – | Weymouth | | 0:5 |
| |
FA Cup 1992/93, First Qualifying Round |
| | | Chippenham Town | – | Thatcham Town | | 1:2 |
| |
FA Cup 1991/92, Preliminary Round |
| | | Bridgend Town | – | Chippenham Town | | 2:0 |
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FA Cup 1990/91, First Qualifying Round |
| | | AFC Lymington | – | Chippenham Town | | 1:0 * |
| |
FA Cup 1989/90, First Qualifying Round |
| | | Chippenham Town | – | Weston-Super-Mare | | 1:2 |
| |
FA Cup 1988/89, First Qualifying Round |
| | | Waterlooville | – | Chippenham Town | | 2:0 |
| |
FA Cup 1987/88, Preliminary Round |
| | | Ottery St Mary | – | Chippenham Town | | 1:0 |
| |
FA Cup 1986/87, Second Qualifying Round |
| | | Chippenham Town | – | Wimborne Town | | 0:1 * |
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FA Cup 1985/86, Third Qualifying Round |
| | | Chippenham Town | – | Barry Town |  | 0:1 * |
| |
FA Cup 1984/85, Fourth Qualifying Round |
| | | Farnborough Town | – | Chippenham Town | | 2:1 |
| |
FA Cup 1983/84, Preliminary Round |
| | | Chippenham Town | – | Romsey Town | | 0:1 * |
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FA Cup 1982/83, First Qualifying Round |
| | | Basingstoke Town | – | Chippenham Town | | 3:2 * |
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FA Cup 1981/82, Preliminary Round |
| | | Hungerford Town | – | Chippenham Town | | 4:0 |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Chippenham Town | – | Lye Town | | 0:2 * |
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FA Cup 1979/80, First Qualifying Round |
| | | Chippenham Town | – | Merthyr Tydfil | | 0:3 |
| |
FA Cup 1978/79, First Qualifying Round |
| | | Cinderford Town | – | Chippenham Town | | 2:1 * |
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FA Cup 1977/78, First Qualifying Round |
| | | Calne Town | – | Chippenham Town | | 3:1 |
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FA Cup 1976/77, First Qualifying Round |
| | | Chippenham Town | – | Devizes Town | | 1:3 |
| |
FA Cup 1975/76, First Qualifying Round |
| | | Chippenham Town | – | Cinderford Town | | 2:4 |
| |
FA Cup 1974/75, Second Qualifying Round |
| | | Chippenham Town | – | Mangotsfield United | | 0:2 |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Melksham Town | – | Chippenham Town | | 4:2 |
| |
FA Cup 1972/73, First Qualifying Round |
| | | Chippenham Town | – | Devizes Town | | 0:4 |
| |
FA Cup 1971/72, First Qualifying Round |
| | | Bath City | – | Chippenham Town | | 2:1 |
| |
FA Cup 1970/71, Preliminary Round |
| | | Poole Town | – | Chippenham Town | | 4:0 |
| |
FA Cup 1969/70, Third Qualifying Round |
| | | Glastonbury | – | Chippenham Town | | 7:0 * |
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FA Cup 1968/69, First Qualifying Round |
| | | Chippenham Town | – | Welton Rovers | | 2:4 |
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FA Cup 1967/68, Second Qualifying Round |
| | | Dorchester Town | – | Chippenham Town | | 4:1 |
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FA Cup 1966/67, Second Qualifying Round |
| | | Chippenham Town | – | Welton Rovers | | 0:4 |
| |
FA Cup 1965/66, Second Qualifying Round |
| | | Cheltenham Town | – | Chippenham Town | | 4:1 |
| |
FA Cup 1964/65, First Qualifying Round |
| | | Trowbridge Town | – | Chippenham Town | | 3:1 |
| |
FA Cup 1963/64, Second Qualifying Round |
| | | Chippenham Town | – | Trowbridge Town | | 2:4 * |
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FA Cup 1962/63, Third Qualifying Round |
| | | Chippenham Town | – | Trowbridge Town | | 0:1 |
| |
FA Cup 1961/62, Third Qualifying Round |
| | | Cheltenham Town | – | Chippenham Town | | 2:0 |
| |
FA Cup 1960/61, First Qualifying Round |
| | | Chippenham Town | – | Trowbridge Town | | 0:1 * |
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FA Cup 1959/60, First Qualifying Round |
| | | Westbury United | – | Chippenham Town | | 3:1 |
| |
FA Cup 1958/59, Third Qualifying Round |
| | | Trowbridge Town | – | Chippenham Town | | 3:0 * |
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FA Cup 1957/58, Second Qualifying Round |
| | | Trowbridge Town | – | Chippenham Town | | 3:0 * |
| |
FA Cup 1956/57, Fourth Qualifying Round |
| | | Weymouth | – | Chippenham Town | | 4:1 * |
| |
FA Cup 1955/56, First Qualifying Round |
| | | Chippenham Town | – | Westbury United | | 0:1 * |
| |
FA Cup 1954/55, Preliminary Round |
| | | Frome Town | – | Chippenham Town | | 4:2 |
| |
FA Cup 1953/54, Fourth Qualifying Round |
| | | Chippenham Town | – | Weymouth | | 2:4 |
| |
FA Cup 1952/53, Second Qualifying Round |
| | | Salisbury | – | Chippenham Town | | 3:1 |
| |
FA Cup 1951/52, First Round Proper |
| 24.11.1951 | | Leyton | – | Chippenham Town | | 3:0 |
| |
FA Cup 1950/51, Preliminary Round |
| | | Bath City | – | Chippenham Town | | 2:0 |
| |
FA Cup 1949/50, First Qualifying Round |
| | | Trowbridge Town | – | Chippenham Town | | 3:1 |
| |
FA Cup 1947/48, Preliminary Round |
| | | Westbury United | – | Chippenham Town | | 3:0 |
| |
FA Cup 1946/47, Preliminary Round |
| | | Trowbridge Town | – | Chippenham Town | | 6:0 |
| |
FA Cup 1945/46, Second Qualifying Round |
| | | Trowbridge Town | – | Chippenham Town | | 3:1 |
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