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| FOOTBALL LEAGUE TROPHY | |||||||||||||||||
| Year | Round | Home | Away | P | W | D | L | GF | GA | Win | Draw | Loss | Gills Gls | Away Gls | |||
| 44 | 13 | 10 | 21 | 58 | 69 | ||||||||||||
| LDV Vans Trophy | |||||||||||||||||
| 2005/2006 | 2nd Rd South | Gillingham | 2-2 | Wycombe Wanderers | aet | 0 | 1 | 0 | 2 | 2 | |||||||
| Wycombe won 3-1 on penalties | |||||||||||||||||
| 1st Rd South | Gillingham | 2-0 | Crawley Town | aet | 1 | 0 | 0 | 2 | 0 | ||||||||
| 2000 - 2005 | Not entered | ||||||||||||||||
| Auto Windscreens Shield | |||||||||||||||||
| 1999/2000 | 1st Rd South | Gillingham | 0-3 | Torquay United | 0 | 0 | 1 | 0 | 3 | ||||||||
| 1998/1999 | Semi-Final South | Millwall | 1-0 | Gillingham | 0 | 0 | 1 | 0 | 1 | ||||||||
| Quarter Final South | Swansea City | 0-1 | Gillingham | 1 | 0 | 0 | 1 | 0 | |||||||||
| 2nd Rd South | Colchester United | 1-5 | Gillingham | 1 | 0 | 0 | 5 | 1 | |||||||||
| 1st Rd South | Torquay United | 0-1 | Gillingham | 1 | 0 | 0 | 1 | 0 | |||||||||
| 1997/1998 | 1st Rd South | Gillingham | 0-1 | Peterborough United | 0 | 0 | 1 | 0 | 1 | ||||||||
| 1996/1997 | 1st Rd South | Gillingham | 1-2 | Cardiff City | 0 | 0 | 1 | 1 | 2 | ||||||||
| 1995/1996 | Southern Section | Cardiff City | 3-2 | Gillingham | 0 | 0 | 1 | 2 | 3 | ||||||||
| Southern Section | Gillingham | 2-2 | Hereford United | 0 | 1 | 0 | 2 | 2 | |||||||||
| 1994/1995 | Southern Section | Gillingham | 1-1 | Brighton & Hove Albion | 0 | 1 | 0 | 1 | 1 | ||||||||
| Southern Section | Brentford | 3-1 | Gillingham | 0 | 0 | 1 | 1 | 3 | |||||||||
| 1st Rd South | Birmingham City | 3-0 | Gillingham | 0 | 0 | 1 | 0 | 3 | |||||||||
| Autoglass Trophy | |||||||||||||||||
| 1993/1994 | Southern Section | Gillingham | 0-0 | Colchester United | 0 | 1 | 0 | 0 | 0 | ||||||||
| Southern Section | Cambridge United | 2-0 | Gillingham | 0 | 0 | 1 | 0 | 2 | |||||||||
| 1992/1993 | Southern Section | Gillingham | 3-3 | Fulham | 0 | 1 | 0 | 3 | 3 | ||||||||
| Southern Section | Leyton Orient | 4-1 | Gillingham | 0 | 0 | 1 | 1 | 4 | |||||||||
| 1991/1992 | Southern Section | Fulham | 2-0 | Gillingham | 0 | 0 | 1 | 0 | 2 | ||||||||
| Southern Section | Gillingham | 4-2 | Maidstone United | 1 | 0 | 0 | 4 | 2 | |||||||||
| 1st Rd South | Fulham | 2-0 | Gillingham | 0 | 0 | 1 | 0 | 2 | |||||||||
| Leyland DAF Cup | |||||||||||||||||
| 1990/1991 | Southern Section | Bournemouth | 0-0 | Gillingham | 0 | 1 | 0 | 0 | 0 | ||||||||
| Southern Section | Gillingham | 4-1 | Maidstone United | 1 | 0 | 0 | 4 | 1 | |||||||||
| 1st Rd South | Gillingham | 0-1 | Hereford United | 0 | 0 | 1 | 0 | 1 | |||||||||
| 1989/1990 | Southern Section | Southend United | 1-0 | Gillingham | 0 | 0 | 1 | 0 | 1 | ||||||||
| Southern Section | Gillingham | 2-0 | Cambridge United | 1 | 0 | 0 | 2 | 0 | |||||||||
| 1st Rd South | Bristol Rovers | 1-0 | Gillingham | 0 | 0 | 1 | 0 | 1 | |||||||||
| Sherpa Van Trophy | |||||||||||||||||
| 1988/1989 | Southern Section | Brentford | 2-0 | Gillingham | 0 | 0 | 1 | 0 | 2 | ||||||||
| Southern Section | Gillingham | 2-1 | Fulham | 1 | 0 | 0 | 2 | 1 | |||||||||
| 1st Rd South | Torquay United | 3-0 | Gillingham | 0 | 0 | 1 | 0 | 3 | |||||||||
| 1987/1988 | Southern Section | Aldershot Town | 3-1 | Gillingham | 0 | 0 | 1 | 1 | 3 | ||||||||
| Southern Section | Gillingham | 2-2 | Leyton Orient | 0 | 1 | 0 | 2 | 2 | |||||||||
| Freight Rover Trophy | |||||||||||||||||
| 1986/1987 | Southern Section | Notts County | 0-5 | Gillingham | 1 | 0 | 0 | 5 | 0 | ||||||||
| Southern Section | Gillingham | 1-0 | Northampton Town | 1 | 0 | 0 | 1 | 0 | |||||||||
| 1st Rd South | Gillingham | 2-0 | Colchester United | 1 | 0 | 0 | 2 | 0 | |||||||||
| Quarter-Final South | Port Vale | 3-3 | Gillingham | 0 | 1 | 0 | 3 | 3 | |||||||||
| Gills won 5-4 on penalties | |||||||||||||||||
| Semi-Final South | Bristol City | 2-0 | Gillingham | 0 | 0 | 1 | 0 | 2 | |||||||||
| 1985/1986 | Southern Section | Derby County | 0-2 | Gillingham | 1 | 0 | 0 | 2 | 0 | ||||||||
| Southern Section | Gillingham | 1-1 | Brentford | 0 | 1 | 0 | 1 | 1 | |||||||||
| Quarter-Final South | Gillingham | 2-0 | Cambridge United | 1 | 0 | 0 | 2 | 0 | |||||||||
| Semi-Final South | Bristol City | 3-0 | Gillingham | 0 | 0 | 1 | 0 | 3 | |||||||||
| 1984/1985 | 1st Rd 1st Leg South | Gillingham | 2-2 | Colchester United | 0 | 1 | 0 | 2 | 2 | ||||||||
| 1st Rd 2nd Leg South | Colchester United | 2-0 | Gillingham | 0 | 0 | 1 | 0 | 2 | |||||||||
| Associate Members Trophy | |||||||||||||||||
| 1983/1984 | 1st Rd South | Millwall | 4-3 | Gillingham | 0 | 0 | 1 | 3 | 4 | ||||||||
| 44 | 13 | 10 | 21 | 58 | 69 | ||||||||||||