1999–2000 Gillingham F.C. season
The 1999–2000 season was Gillingham F.C.'s sixty-eighth season in the Football League. They gained promotion to the Football League First Division, after beating Wigan Athletic in the 2000 Football League Second Division play-off Final. Gillingham also had a successful FA Cup run, reaching the sixth round before being knocked out by Chelsea.
Football League Second Division
| Date | Opponents | H / A | Result F – A | Scorers | Attendance |
| 7 August 1999 | Bury | A | 1 – 2 | Thomson 76' | 4,014 |
| 14 August 1999 | Bristol Rovers | H | 0 – 1 | 6,234 | |
| 21 August 1999 | Blackpool | A | 1 – 1 | Ashby 40' | 4,203 |
| 28 August 1999 | Wycombe Wanderers | H | 2 – 2 | Taylor 37', McGlinchey 86' | 6,180 |
| 30 August 1999 | Stoke City | A | 1 – 1 | Taylor 90' | 8,369 |
| 4 September 1999 | Oldham Athletic | H | 2 – 1 | Taylor 4', Omoyinmi 6' | 5,884 |
| 11 September 1999 | Oxford United | A | 2 – 1 | Southall 53', Omoyinmi 90' | 5,418 |
| 18 September 1999 | Preston North End | H | 0 – 2 | 6,610 | |
| 25 September 1999 | Cambridge United | A | 2 – 2 | Taylor 26', Butters 69' | 4,708 |
| 2 October 1999 | Millwall | H | 2 – 0 | Lewis 22', Taylor 63' | 6,616 |
| 9 October 1999 | Wrexham | H | 5 – 1 | Thomson 26', Southall 45', Taylor 65', 67', 70' | 5,997 |
| 16 October 1999 | Luton Town | A | 1 – 3 | Lewis 16' | 6,394 |
| 19 October 1999 | Brentford | A | 2 – 1 | Omoyinmi 27', Saunders 29' | 6,264 |
| 23 October 1999 | Cambridge United | H | 2 – 1 | Thomson 47', 84' | 6,417 |
| 2 November 1999 | Bristol City | H | 3 – 0 | Taylor 60', 63', 89' | 6,892 |
| 6 November 1999 | Notts County | A | 1 – 1 | Taylor 20' | 6,023 |
| 12 November 1999 | Bournemouth | H | 4 – 1 | Hessenthaler 12', Thomson 19', Taylor 50', 59' | 6,336 |
| 23 November 1999 | Scunthorpe United | A | 4 – 1 | Taylor 24', Thomson 33', Lewis 52', Nosworthy 76' | 3,444 |
| 27 November 1999 | Cardiff City | A | 2 – 1 | Hessenthaler 1', Thomson 21' | 7,608 |
| 4 December 1999 | Bury | H | 1 – 0 | Edge 62' | 7,036 |
| 26 December 1999 | Colchester United | H | 2 – 1 | Rowe 13', Southall 42' | 7,338 |
| 28 December 1999 | Wigan Athletic | A | 0 – 2 | 8,054 | |
| 3 January 2000 | Reading | H | 2 – 2 | Southall 20', Thomson 90' | 7,453 |
| 15 January 2000 | Bristol Rovers | A | 1 – 2 | Onuora 88' | 8,331 |
| 22 January 2000 | Blackpool | H | 1 – 3 | Southall 52' | 6,805 |
| 1 February 2000 | Chesterfield | A | 0 – 0 | 2,898 | |
| 5 February 2000 | Stoke City | H | 3 – 0 | Onuora 13', Gooden 32', Rowe 73' | 7,801 |
| 12 February 2000 | Oldham Athletic | A | 3 – 1 | Gooden 4', Ashby 41', Rowe 67' | 5,144 |
| 26 February 2000 | Preston North End | A | 2 – 0 | Asaba 58', 69' | 13,246 |
| 4 March 2000 | Oxford United | H | 1 – 0 | Lewis 89' | 6,966 |
| 7 March 2000 | Notts County | H | 0 – 1 | 6,915 | |
| 11 March 2000 | Bristol City | A | 1 – 0 | Hessenthaler 78' | 9,332 |
| 14 March 2000 | Burnley | H | 2 – 2 | Butters 4', Asaba 68' | 7,347 |
| 18 March 2000 | Scunthorpe United | H | 3 – 1 | Lewis 34', Thomson 55', Southall 73' | 6,822 |
| 21 March 2000 | Bournemouth | A | 1 – 0 | Onuora 44' | 4,443 |
| 25 March 2000 | Colchester United | A | 1 – 2 | Rowe 79' | 4,337 |
| 28 March 2000 | Wycombe Wanderers | A | 0 – 1 | 4,183 | |
| 1 April 2000 | Chesterfield | H | 1 – 0 | Butler 75' | 6,772 |
| 7 April 2000 | Reading | A | 2 – 2 | Southall 49', Onuora 65' | 11,064 |
| 15 April 2000 | Wigan Athletic | H | 2 – 1 | Onuora 18', Lewis 82' | 7,746 |
| 18 April 2000 | Burnley | A | 3 – 0 | Gooden 21', Ashby 50', Smith 70' | 17,026 |
| 22 April 2000 | Luton Town | H | 2 – 0 | Hessenthaler 9', Southall 60' | 8,667 |
| 24 April 2000 | Millwall | A | 2 – 2 | Gooden 11', Hessenthaler 40' | 17,929 |
| 29 April 2000 | Brentford | H | 2 – 0 | Onuora 37', Butler 87' | 9,001 |
| 2 May 2000 | Cardiff City | H | 4 – 1 | Asaba 11', 36', 59', Southall 27' | 9,178 |
| 6 May 2000 | Wrexham | A | 0 – 1 | 8,811 |
Colours: Green = Gillingham win; Yellow = draw; Red = away team win.
| Pos | Club | Pld | W | D | L | F | A | GD | Pts |
| 1 | Preston North End ' | 46 | 28 | 11 | 7 | 74 | 37 | +37 | 95 |
| 2 | Burnley ' | 46 | 25 | 13 | 8 | 69 | 47 | +22 | 88 |
| 3 | Gillingham | 46 | 25 | 10 | 11 | 79 | 48 | +31 | 85 |
| 4 | Wigan Athletic | 46 | 22 | 17 | 7 | 72 | 38 | +34 | 83 |
| 5 | Millwall | 46 | 23 | 13 | 10 | 76 | 50 | +26 | 82 |
| 6 | Stoke City | 46 | 23 | 13 | 10 | 68 | 42 | +26 | 82 |
Pld = Matches played; W = Matches won; D = Matches drawn; L = Matches lost; F = Goals for; A = Goals against; GD = Goal difference; Pts = Points
Source:
Play-offs
FA Cup
| Date | Round | Opponents | H / A | Result F – A | Scorers | Attendance |
| 30 October 1999 | First Round | Cheltenham Town | A | 1 – 1 | Southall 37' | 3,188 |
| 9 November 1999 | First Round Replay | Cheltenham Town | H | 3 – 2 | Thomson 24', Pennock 41', McGlinchey 77' | 4,352 |
| 20 November 1999 | Second Round | Darlington | H | 3 – 1 | Butters 17', Taylor 43', 47' | 5,168 |
| 11 December 1999 | Third Round | Walsall | A | 1 – 1 | Southall 27' | 4,314 |
| 8 January 2000 | Third Round Replay | Walsall | H | 2 – 1 | Barras 38', Thomson 100' | 6,538 |
| 11 January 2000 | Fourth Round | Bradford City | H | 3 – 1 | Thomson 39', Ashby 54', Hodge 78' | 7,091 |
| 29 January 2000 | Fifth Round | Sheffield Wednesday | H | 3 – 1 | Saunders 70', Thomson 72', Southall 82' | 10,130 |
| 20 February 2000 | Sixth Round | Chelsea | A | 0 – 5 | 34,205 |
Colours: Green = Gillingham win; Yellow = draw; Red = away team win.
League Cup
| Date | Round | Opponents | H / A | Result F – A | Scorers | Attendance |
| 11 August 1999 | First Round First Leg | Brighton & Hove Albion | A | 2 – 0 | Ormerod 45', Hessenthaler 67' | 5,613 |
| 24 August 1999 | First Round Second Leg | Brighton & Hove Albion | H | 2 – 0 | Taylor 19', Southall 31' | 4,592 |
| 14 September 1999 | Second Round First Leg | Bolton Wanderers | H | 1 – 4 | Hessenthaler 55' | 4,996 |
| 21 September 1999 | Second Round Second Leg | Bolton Wanderers | A | 0 – 2 | 3,673 |
Colours: Green = Gillingham win; Yellow = draw; Red = away team win.