Johnstone's Paint Trophy 2009-10 Winners: Southampton Runners-up: Carisle United Winners from previous season: Luton Town First round
| Northern section | Grimsby Town, Hartlepool United, Leeds United, Macclesfield Town, Notts County, Port Vale, Shrewsbury Town and Tranmere Rovers given byes to the second round. | 1 September 2009 | Burton Albion | 1 | - | 5 | Chesterfield | 1,493 | Pirelli Stadium, Burton-on-Trent | 1 September 2009 | Crewe Alexandra | 1 | - | 4 | Stockport County | 2,331 | Gresty Road, Crewe | 1 September 2009 | Darlington | 1 | - | 0 | Lincoln City | 828 | Darlington Arena, Darlington | 1 September 2009 | Morecambe | 2 | - | 2 | Carlisle United (won 4-2 on pens.) | 2,106 | Christie Park, Morecambe | 1 September 2009 | Oldham Athletic | 1 | - | 2 | Accrington Stanley | 1,619 | Boundary Park, Oldham | 1 September 2009 | Rochdale | 1 | - | 2 | Bradford City | 1,800 | Spotland, Rochdale | 1 September 2009 | Rotherham United | 1 | - | 2 | Huddersfield Town | 2,246 | Don Valley Stadium, Rotherham | 1 September 2009 | Walsall | 0 | - | 0 | Bury (won 5-4 on pens.) | 2,314 | Bescot Stadium, Walsall | Southern Section
| Aldershot Town, Brighton & Hove Albion, Charlton Athletic, Exeter City, Leyton Orient, Southampton, Southend United and Swindon Town given byes to the second round. | 1 September 2009 | AFC Bournemouth | 2 | - | 1 | Yeovil Town | 2,655 | Fitness First Stadium, Bournemouth | 1 September 2009 | Barnet | 2 | - | 0 | Millwall | 1,623 | Underhill, London | 1 September 2009 | Cheltenham Town | 1 | - | 3 | Torquay United | 1,397 | Whaddon Road, Cheltenham | 1 September 2009 | Gillingham (won 4-3 on pens.) | 1 | - | 1 | Colchester United | 1,725 | Priestfield, Gillingham | 1 September 2009 | Hereford United (won 4-2 on pens.) | 0 | - | 0 | Bristol Rovers | 970 | Edgar Street, Hereford | 1 September 2009 | Milton Keynes Dons | 3 | - | 1 | Dagenham & Redbridge | 4,413 | Stadium: MK, Milton Keynes | 1 September 2009 | Norwich City | 1 | - | 0 | Brentford | 12,540 | Carrow Road, Norwich | 1 September 2009 | Wycombe Wanderers | 2 | - | 2 | Northampton Town (won 3-0 on pens.) | 1,035 | Adams Park, High Wycombe | Second round | Northern section | 6 October 2009 | Bradford City (won 3-2 on pens.) | 2 | - | 2 | Notts County | 3,701 | Valley Parade, Bradford | 6 October 2009 | Bury | 2 | - | 1 | Tranmere Rovers | 1,903 | Gigg Lane, Bury | 6 October 2009 | Carlisle United | 4 | - | 2 | Macclesfield Town | 1,753 | Brunton Park, Carlisle | 6 October 2009 | Chesterfield (won 4-2 on pens.) | 3 | - | 3 | Huddersfield Town | 3,003 | Recreation Ground, Chesterfield | 6 October 2009 | Hartlepool United | 0 | - | 2 | Grimsby Town | 1,675 | Victoria Park, Hartlepool | 6 October 2009 | Leeds United | 2 | - | 1 | Darlington | 8,429 | Elland Road, Leeds | 6 October 2009 | Port Vale | 3 | - | 1 | Stockport County | 3,154 | Vale Park, Burslem | 20 October 2009 | Accrington Stanley | 2 | - | 0 | Shrewsbury Town | 891 | Crown Ground, Accrington | Southern section | 6 October 2009 | Charlton Athletic | 4 | - | 1 | Barnet | 4,522 | The Valley, London | 6 October 2009 | Exeter City | 1 | - | 1 | Swindon Town (won 4-3 on pens.) | 2,006 | St James's Park, Exeter | 6 October 2009 | Gillingham | 0 | - | 1 | Norwich City | 2,814 | Priestfield, Gillingham | 6 October 2009 | Hereford United (won 4-3 on pens.) | 2 | - | 2 | Aldershot Town | 897 | Edgar Street, Hereford | 6 October 2009 | Leyton Orient | 1 | - | 0 | Brighton & Hove Albion | 1,457 | Brisbane Road, London | 6 October 2009 | Milton Keynes Dons | 2 | - | 0 | Southed United | 4,792 | Stadium: MK, Milton Keynes | 6 October 2009 | Northampton Town | 2 | - | 1 | AFC Bournemouth | 1,718 | Sixfields Stadium, Northampton | 6 October 2009 | Southampton (won 5-3 on pens.) | 2 | - | 2 | Torquay United | 9,319 | St Mary's Stadium, Southampton | Quarter-finals | Northern section | 10 November 2009 | Accrington Stanley | 3 | - | 2 | Bury | 1,637 | Crown Ground, Accrington | 10 November 2009 | Bradford City (won 5-3 on pens.) | 2 | - | 2 | Port Vale | 5,096 | Valley Parade, Bradford | 10 November 2009 | Chesterfield | 1 | - | 3 | Carlisle United | 2,878 | Recreation Park, Chesterfield | 10 November 2009 | Leeds United | 3 | - | 1 | Grimsby Town | 10,430 | Elland Road, Leeds | Southern section | 10 November 2009 | Leyton Orient | 1 | - | 1 | Hereford United (won 3-2 on pens.) | 1,282 | Brisbane Road, London | 10 November 2009 | Milton Keynes Dons | 3 | - | 1 | Northampton Town | 8,886 | Stadium: MK, Milton Keynes | 10 November 2009 | Swindon Town | 0 | - | 0 | Norwich City (won 5-3 on pens.) | 4,978 | County Ground, Swindon | 11 November 2009 | Southampton | 2 | - | 1 | Charlton Athletic | 13,906 | St Mary's Stadium, Southampton | Semi-Finals | Northern section | 15 December 2009 | Carlisle United | 3 | - | 0 | Bradford City | 3,176 | Valley Parade, Bradford | 15 December 2009 | Leeds United | 2 | - | 0 | Accrington Stanley | 12,696 | Elland Road, Leeds | Southern section | 15 December 2009 | Hereford United | 1 | - | 4 | Milton Keynes Dons | 1,367 | Edgar Street, Hereford | 15 December 2009 | Southampton (won 6-5 on pens.) | 2 | - | 2 | Norwich City | 15,453 | St Mary's Stadium, Southampton | Area Finals | Northern section: 1st leg | 19 January 2010 | Leeds United | 1 | - | 2 | Carlisle United | 13,011 | Elland Road, Leeds | Southern section: 1st leg | 20 January 2010 | Milton Keynes Dons | 0 | - | 1 | Southampton | 7,918 | Stadium: MK, Milton Keynes | Northern section: 2nd leg | 9 February 2010 | Carlisle United | 2 | - | 3 | Leeds United | 9,430 | Brunton Park, Carlisle | (4-4 on aggregate; Carlisle United win 6-5 on pens.) | Southern section: 2nd leg | 9 February 2010 | Southampton | 3 | - | 1 | Milton Keynes Dons | 29,901 | St Mary's Stadium, Southampton | (Southampton win 4-1 on aggregate) | National final | 28 March 2010 | Southampton | 3 | - | 1 | Carlisle United | 73,476 | Wembley Stadium, London |
|