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 2020/21, Second round |
| 15.09.2020 | | Millwall | – | Cheltenham Town | | 3:1 (1:0) * |
| London |
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 2017/18, Second round |
| 23.08.2017 | | Cheltenham Town | – | West Ham United | | 0:2 (0:2) |
| Cheltenham |
Football League Cup 2016/17, Second round |
| 23.08.2016 | | Newcastle United | – | Cheltenham Town | | 2:0 (1:0) |
| Newcastle upon Tyne |
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 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 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 2005/06, Second round |
| 20.09.2005 | | Sunderland | – | Cheltenham Town | | 1:0 aet
(0:0) |
| Sunderland |
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 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 1999/00, First Round |
| 10.08.1999 | | Norwich City | – | Cheltenham Town | | 2:0 (2:0) |
| Norwich |
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