Football League Cup 2023/24, First Round |
 | 08.08.2023 | | Cheltenham Town | – | Birmingham City | | 0:2 (0:2) |
| Cheltenham |
Football League Cup 2022/23, First Round |
| 09.08.2022 | | Cheltenham Town | – | Exeter City | | 0:7 (0:5) |
| Cheltenham |
Football League Cup 2021/22, Third round |
| 21.09.2021 | | Preston North End | – | Cheltenham Town | | 4:1 (2:0) |
| Preston |
Football League Cup 2021/22, Second round |
| 24.08.2021 | | Gillingham | – | Cheltenham Town | | 1:1 (1:1),
pen. 4:5 |
| Gillingham |
Football League Cup 2021/22, First Round |
| 10.08.2021 | | Bristol Rovers | – | Cheltenham Town | | 0:2 (0:0) |
| Bristol |
Football League Cup 2020/21, Second round |
| 15.09.2020 | | Millwall | – | Cheltenham Town | | 3:1 (1:0) * |
| London |
Football League Cup 2020/21, First Round |
| 05.09.2020 | | Peterborough United | – | Cheltenham Town | | 0:1 (0:0) * |
| Peterborough |
Football League Cup 2019/20, First Round |
| 13.08.2019 | | Bristol Rovers | – | Cheltenham Town | | 3:0 (1:0) |
| Bristol |
Football League Cup 2018/19, Second round |
| 28.08.2018 | | Brentford | – | Cheltenham Town | | 1:0 (1:0) |
| Brentford |
Football League Cup 2018/19, First Round |
| 14.08.2018 | | Cheltenham Town | – | Colchester United | | 2:2 (1:0),
pen. 6:5 |
| Cheltenham |
Football League Cup 2017/18, Second round |
| 23.08.2017 | | Cheltenham Town | – | West Ham United | | 0:2 (0:2) |
| Cheltenham |
Football League Cup 2017/18, First Round |
| 08.08.2017 | | Oxford United | – | Cheltenham Town | | 3:4 aet
(3:1, 3:3) |
| Oxford |
Football League Cup 2016/17, Second round |
| 23.08.2016 | | Newcastle United | – | Cheltenham Town | | 2:0 (1:0) |
| Newcastle upon Tyne |
Football League Cup 2016/17, First Round |
| 09.08.2016 | | Cheltenham Town | – | Charlton Athletic | | 1:0 (1:0) |
| Cheltenham |
Football League Cup 2014/15, First Round |
| 12.08.2014 | | Brighton & Hove Albion | – | Cheltenham Town | | 2:0 (0:0) |
| Brighton & Hove |
Football League Cup 2013/14, Second round |
| 27.08.2013 | | West Ham United | – | Cheltenham Town | | 2:1 (1:0) |
| London |
Football League Cup 2013/14, First Round |
| 06.08.2013 | | Cheltenham Town | – | Crawley Town | | 4:3 aet
(1:1, 3:3) |
| Cheltenham |
Football League Cup 2012/13, First Round |
| 11.08.2012 | | Cheltenham Town | – | Milton Keynes Dons | | 1:1 aet
(0:1, 1:1) |
| Cheltenham |
Football League Cup 2011/12, First Round |
| 09.08.2011 | | Cheltenham Town | – | Milton Keynes Dons | | 1:4 (1:1) |
| Cheltenham |
Football League Cup 2010/11, First Round |
| 10.08.2010 | | Brentford | – | Cheltenham Town | | 2:1 (2:0) |
| Brentford |
Football League Cup 2009/10, First Round |
| 11.08.2009 | | Cheltenham Town | – | Southend United | | 1:2 (1:0) |
| Cheltenham |
Football League Cup 2008/09, Second round |
| 26.08.2008 | | Cheltenham Town | – | Stoke City | | 2:3 (0:0) |
| Cheltenham |
Football League Cup 2008/09, First Round |
| 12.08.2008 | | Southend United | – | Cheltenham Town | | 0:1 aet
(0:0) |
| Southend-on-Sea |
Football League Cup 2007/08, First Round |
| 14.08.2007 | | Southend United | – | Cheltenham Town | | 4:1 aet
(1:0, 1:1) |
| Southend-on-Sea |
Football League Cup 2006/07, Second round |
| 19.09.2006 | | West Bromwich Albion | – | Cheltenham Town | | 3:1 (0:1) |
| West Bromwich |
Football League Cup 2006/07, First Round |
| 22.08.2006 | | Cheltenham Town | – | Bristol City | | 2:1 (2:1) |
| Cheltenham |
Football League Cup 2005/06, Second round |
| 20.09.2005 | | Sunderland | – | Cheltenham Town | | 1:0 aet
(0:0) |
| Sunderland |
Football League Cup 2005/06, First Round |
| 23.08.2005 | | Cheltenham Town | – | Brentford | | 5:0 (1:0) |
| Cheltenham |
Football League Cup 2004/05, First Round |
| 24.08.2004 | | Colchester United | – | Cheltenham Town | | 2:1 (1:0) |
| Colchester |
Football League Cup 2003/04, First Round |
| 12.08.2003 | | Cheltenham Town | – | Queens Park Rangers | | 1:2 (1:1) |
| Cheltenham |
Football League Cup 2002/03, Second round |
| 02.10.2002 | | Crystal Palace | – | Cheltenham Town | | 7:0 (1:0) |
| London |
Football League Cup 2002/03, First Round |
| 10.09.2002 | | Norwich City | – | Cheltenham Town | | 0:3 (0:2) |
| Norwich |
Football League Cup 2001/02, First Round |
| 21.08.2001 | | Bristol City | – | Cheltenham Town | | 2:1 (1:0) |
| Bristol |
Football League Cup 2000/01, First Round |
| 05.09.2000 | | Cheltenham Town | – | Watford | | 0:3 (0:2) |
| Cheltenham |
Football League Cup 2000/01, First Round |
| 22.08.2000 | | Watford | – | Cheltenham Town | | 0:0 |
| Watford |
Football League Cup 1999/00, First Round |
| 24.08.1999 | | Cheltenham Town | – | Norwich City | | 2:1 aet
(0:0, 2:0) |
| Cheltenham |
Football League Cup 1999/00, First Round |
| 10.08.1999 | | Norwich City | – | Cheltenham Town | | 2:0 (2:0) |
| Norwich |
Superclásico
Copa Newton
Copa Lipton
Copa Rosa
Copa Félix Bogado
Copa Carlos Dittborn
Copa Ramón Castilla
Copa Rio Branco
Copa Rodrigues Alves
Taça Bernardo O'Higgins
Copa Artigas
Copa Paz del Chaco
Copa del Pacífico
