| Club: | Charlton Athletic |
| Season: | 1999–2000 |
| Manager: | Alan Curbishley |
| Chairman: | Richard Murray |
| Stadium: | The Valley |
| League: | First Division |
| League Result: | 1st (promoted) |
| Cup1: | FA Cup |
| Cup1 Result: | Sixth round |
| Cup2: | Worthington Cup |
| Cup2 Result: | Second round |
| League Topscorer: | Hunt (24) |
| Season Topscorer: | Hunt (25) |
| Lowest Attendance: | 18,663 Walsall (6 November 1999) |
| Average Attendance: | 19,558 |
| Prevseason: | 1998–99 |
| Nextseason: | 2000–01 |
During the 1999–2000 English football season, Charlton Athletic F.C. competed in the Football League First Division.
Alan Curbishley and his Charlton side won the First Division title to regain promotion to the FA Carling Premiership for the 2000-2001 season at the first time of asking.
A key player in the previous season's unsuccessful bid to avoid relegation, Richard Rufus remained with the club and enjoyed a very productive season scoring six goals and helping Charlton to win the First Division title.
Charlton Athletic's score comes first
| Win | Draw | Loss |
| Date | Opponent | Venue | Result | Attendance | Scorers | |
|---|---|---|---|---|---|---|
| 7 August 1999 | Barnsley | H | 3-1 | 19,268 | Mendonca (3, 2 pens) | |
| 21 August 1999 | Norwich City | H | 1-0 | 19,623 | Rufus | |
| 28 August 1999 | Fulham | A | 1-2 | 15,154 | Melville (own goal) | |
| 11 September 1999 | Bolton Wanderers | H | 2-1 | 19,028 | Stuart, Mendonca | |
| 18 September 1999 | Sheffield United | A | 2-1 | 13,216 | Hunt (2) | |
| 25 September 1999 | Tranmere Rovers | A | 2-2 | 5,846 | Mendonca (pen), Kinsella | |
| 28 September 1999 | Stockport County | H | 4-0 | 19,842 | Hunt (3), Mendonca (pen) | |
| 2 October 1999 | Birmingham City | H | 1-0 | 19,753 | Shields | |
| 16 October 1999 | Portsmouth | A | 2-0 | 14,812 | Robinson, Salako | |
| 19 October 1999 | Ipswich Town | A | 2-4 | 17,940 | Hunt (2) | |
| 23 October 1999 | West Bromwich Albion | H | 0-0 | 19,346 | ||
| 26 October 1999 | Tranmere Rovers | H | 3-2 | 19,491 | Brown, Robinson, Rufus | |
| 30 October 1999 | Birmingham City | A | 0-1 | 19,172 | ||
| 2 November 1999 | Crewe Alexandra | A | 2-0 | 4,741 | Stuart, Pringle | |
| 6 November 1999 | Walsall | H | 2-1 | 18,663 | Hunt, Stuart | |
| 12 November 1999 | Grimsby Town | A | 5-2 | 6,849 | Rufus (2), Mendonca, Hunt, Groves (own goal) | |
| 20 November 1999 | Manchester City | H | 0-1 | 20,043 | ||
| 23 November 1999 | Swindon Town | A | 2-1 | 6,515 | Robinson, Newton | |
| 27 November 1999 | Port Vale | H | 2-2 | 19,266 | Mendonca (2) | |
| 30 November 1999 | Blackburn Rovers | H | 1-2 | 18,939 | Newton | |
| 4 December 1999 | Barnsley | A | 1-1 | 14,553 | Jones | |
| 18 December 1999 | Queens Park Rangers | A | 0-0 | 14,709 | ||
| 26 December 1999 | Crystal Palace | H | 2-1 | 20,043 | Salako, Pringle | |
| 28 December 1999 | Huddersfield Town | A | 2-1 | 17,415 | Hunt, Robinson | |
| 3 January 2000 | Nottingham Forest | H | 3-0 | 19,787 | Shields, Stuart, Hunt | |
| 11 January 2000 | Wolverhampton Wanderers | A | 3-2 | 18,464 | Rufus, Pringle, Robinson | |
| 15 January 2000 | Crewe Alexandra | H | 1-0 | 19,125 | Stuart | |
| 22 January 2000 | Norwich City | A | 3-0 | 15,642 | Hunt (3) | |
| 5 February 2000 | Stockport County | A | 3-1 | 8,185 | Hunt (3) | |
| 12 February 2000 | Wolverhampton Wanderers | H | 2-0 | 20,043 | Stuart, Brown | |
| 15 February 2000 | Fulham | H | 1-0 | 19,940 | Robinson | |
| 26 February 2000 | Sheffield United | H | 1-0 | 19,249 | Robinson | |
| 4 March 2000 | Bolton Wanderers | A | 2-0 | 15,000 | Pringle, Hunt | |
| 7 March 2000 | Walsall | A | 4-2 | 6,227 | Hunt (2), Kinsella (2) | |
| 11 March 2000 | Swindon Town | H | 0-1 | 19,569 | ||
| 19 March 2000 | Manchester City | A | 1-1 | 32,139 | Robinson | |
| 22 March 2000 | Grimsby Town | H | 4-0 | 19,364 | Newton, Svensson, Hunt, Tiler | |
| 25 March 2000 | Crystal Palace | A | 1-0 | 22,577 | Kitson | |
| 31 March 2000 | Queens Park Rangers | H | 2-1 | 19,617 | ||
| 4 April 2000 | Port Vale | A | 2-2 | 4,513 | Rufus, Hunt | |
| 8 April 2000 | Nottingham Forest | A | 1-1 | 20,922 | Hunt | |
| 14 April 2000 | Huddersfield Town | H | 0-1 | 19,739 | ||
| 21 April 2000 | Portsmouth | H | 1-1 | 20,043 | Stuart | |
| 24 April 2000 | Blackburn Rovers | A | 1-1 | 18,587 | Svensson | |
| 29 April 2000 | Ipswich Town | H | 1-3 | 20,043 | Hunt | |
| 7 May 2000 | West Bromwich Albion | A | 0-2 | 22,101 |
See main article: 1999–2000 FA Cup.
| R3 | 11 December 1999 | Swindon Town | H | 2-1 | 10,939 | Kinsella (2) | |
| R4 | 8 January 2000 | Queens Park Rangers | H | 1-0 | 16,798 | MacDonald | |
| R5 | 29 January 2000 | Coventry City | A | 3-2 | 23,400 | Robinson, Newton, Hunt | |
| QF | 19 February 2000 | Bolton Wanderers | A | 0-1 | 20,131 |
See main article: 1999–2000 Football League Cup.
| R2 1st Leg | 14 September 1999 | Bournemouth | H | 0-0 | 10,346 | ||
| R2 2nd Leg | 21 September 1999 | Bournemouth | A | 0-0 (lost 1-3 on pens) | 4,369 |
Squad at end of season