| Season: | 1999–2000 |
| Manager: | Colin Todd (until 22 September) Phil Brown (caretaker from 22 September to 19 October) Sam Allardyce (from 19 October) |
| League Topscorer: | Eiður Guðjohnsen Dean Holdsworth (14) |
| Season Topscorer: | Eiður Guðjohnsen (21) |
| Highest Attendance: | 21,671 v Manchester City 28 August 1999 |
| Lowest Attendance: | 3,673 v Gillingham 21 September 1999 |
| Nextseason: | 2000–01 |
The 1999–2000 season was the 121st season in Bolton Wanderers F.C.'s existence, and their second successive season in the Football League First Division. It covers the period from 1 July 1999 to 30 June 2000.[1]
| Date | Opponents | H / A | ResultF – A | Scorers | Attendance | |
|---|---|---|---|---|---|---|
| 7 August 1999 | Tranmere Rovers | A | 0 – 0 | 7,674 | ||
| 14 August 1999 | Queens Park Rangers | H | 2 – 1 | Holdsworth 11' (pen), Guðjohnsen 64' | 13,019 | |
| 21 August 1999 | Ipswich Town | A | 0 – 1 | 17,696 | ||
| 28 August 1999 | Manchester City | H | 0 – 1 | 21,671 | ||
| 5 September 1999 | Birmingham City | H | 3 – 3 | Frandsen (2) 14', 53', Holdsworth 90' (pen) | 11,668 | |
| 11 September 1999 | Charlton Athletic | A | 1 – 2 | Johansen 12' | 19,028 | |
| 18 September 1999 | Barnsley | A | 2 – 2 | Tuttle 4' (og), Gardner 85' | 14,621 | |
| 25 September 1999 | Nottingham Forest | H | 3 – 2 | Gardner 32', Holdsworth 65' (pen), Cox 90' | 14,978 | |
| 2 October 1999 | Swindon Town | A | 4 – 0 | Cox 9', Holdsworth 22', Gardner 26', Elliott 43' | 6,711 | |
| 9 October 1999 | Wolverhampton Wanderers | A | 0 – 1 | 18,665 | ||
| 16 October 1999 | Huddersfield Town | H | 1 – 0 | Gardner 45' | 16,603 | |
| 19 October 1999 | Crewe Alexandra | H | 2 – 2 | Guðjohnsen 44', Holdsworth 58' | 12,676 | |
| 24 October 1999 | Norwich City | A | 1 – 2 | Gardner 74' | 12,468 | |
| 27 October 1999 | Nottingham Forest | A | 1 – 1 | Guðjohnsen 20' | 15,572 | |
| 30 October 1999 | Swindon Town | H | 2 – 0 | Taylor 87', Hansen 88' | 12,486 | |
| 6 November 1999 | Crystal Palace | H | 2 – 0 | Guðjohnsen 64', Jensen 82' | 12,744 | |
| 14 November 1999 | Sheffield United | A | 2 – 1 | Farrelly 2', Hansen 35' | 10,013 | |
| 20 November 1999 | Grimsby Town | H | 2 – 0 | Hansen (2) 50', 69' | 12,415 | |
| 23 November 1999 | Fulham | A | 1 – 1 | Guðjohnsen 15' | 9,642 | |
| 27 November 1999 | Portsmouth | A | 0 – 0 | 10,431 | ||
| 4 December 1999 | Tranmere Rovers | H | 2 – 3 | Guðjohnsen 64', Taylor 77' | 13,534 | |
| 7 December 1999 | Blackburn Rovers | A | 1 – 3 | Elliott 57' | 21,046 | |
| 18 December 1999 | Stockport County | H | 0 – 1 | 13,285 | ||
| 28 December 1999 | West Bromwich Albion | H | 1 – 1 | Jensen 82' | 16,269 | |
| 3 January 2000 | Walsall | A | 0 – 2 | 6,873 | ||
| 15 January 2000 | Queens Park Rangers | A | 1 – 0 | Jensen 64' | 11,396 | |
| 22 January 2000 | Ipswich Town | H | 1 – 1 | Holdsworth 66' | 11,924 | |
| 5 February 2000 | Blackburn Rovers | H | 3 – 1 | Bergsson 17', Johansen 39', Guðjohnsen 69' | 17,687 | |
| 8 February 2000 | Port Vale | A | 1 – 0 | Guðjohnsen 77' | 5,092 | |
| 12 February 2000 | Birmingham City | A | 1 – 2 | Johnston 20' | 18,426 | |
| 22 February 2000 | Portsmouth | H | 3 – 0 | Taylor 12, Jensen 68', Elliott 77' | 12,672 | |
| 26 February 2000 | Barnsley | A | 1 – 1 | Holdsworth 43' (pen) | 14,604 | |
| 4 March 2000 | Charlton Athletic | H | 0 – 2 | 15,000 | ||
| 7 March 2000 | Crystal Palace | A | 0 – 0 | 15,236 | ||
| 11 March 2000 | Fulham | H | 3 – 1 | Holdsworth (2) 45' (pen), 50', Guðjohnsen 90' | 12,761 | |
| 14 March 2000 | Stockport County | A | 0 – 0 | 6,412 | ||
| 18 March 2000 | Grimsby Town | A | 1 – 0 | Bergsson 39' | 5,289 | |
| 21 March 2000 | Sheffield United | H | 2 – 0 | Johnston 32', O'Kane 45' | 11,891 | |
| 25 March 2000 | Port Vale | H | 2 – 1 | Guðjohnsen 16', Johnston 42' | 12,292 | |
| 5 April 2000 | Manchester City | A | 0 – 2 | 32,927 | ||
| 8 April 2000 | Walsall | H | 4 – 3 | Johansen 2' (pen), Hansen (2) 13', 74, Phillips 25' | 11,777 | |
| 15 April 2000 | West Bromwich Albion | A | 4 – 4 | Hansen 36', Bergsson (2) 55, 90, Guðjohnsen 66' | 12,802 | |
| 22 April 2000 | Huddersfield Town | A | 3 – 0 | Hansen (2) 9', 26', Whitlow 58' | 16,404 | |
| 26 April 2000 | Crewe Alexandra | A | 3 – 1 | Guðjohnsen 15', Holdsworth 71' (pen), Jensen 89' | 8,015 | |
| 3 May 2000 | Wolverhampton Wanderers | H | 2 – 1 | Jensen 60', Guðjohnsen 70' | 18,871 | |
| 7 May 2000 | Norwich City | H | 1 – 0 | Holdsworth 72' | 17,987 |
| Date | Round | Opponents | H / A | ResultF – A | Scorers | Attendance | |
|---|---|---|---|---|---|---|---|
| 14 May 2000 | Semi-Final First Leg | Ipswich Town | H | 2 – 2 | Holdsworth 5', Guðjohnsen 26' | 18,814 | |
| 17 May 2000 | Semi Final Second Leg | Ipswich Town | A | 3 – 5 (aet) 5 – 7 (agg) | Holdsworth (2) 6', 39', Johnston 50' | 21,543 |
| Date | Round | Opponents | H / A | ResultF – A | Scorers | Attendance | |
|---|---|---|---|---|---|---|---|
| 21 December 1999 | Round 3 | Cardiff City | H | 1 – 0 | Guðjohnsen 29' | 5,734 | |
| 8 January 2000 | Round 4 | Grimsby Town | A | 2 – 0 | Guðjohnsen 33', Hansen 54' | 4,270 | |
| 29 January 2000 | Round 5 | Cambridge United | A | 3 – 1 | Bob Taylor (2) 53, 75, Guðjohnsen 86' | 7,523 | |
| 19 February 2000 | Round 6 | Charlton Athletic | H | 1 – 0 | Guðjohnsen 47' | 20,131 | |
| 2 April 2000 | Semi Final | Aston Villa | Wembley Stadium | 0 – 0 (aet) Aston Villa won 4 – 1 on penalties | 62,828 |
| Date | Round | Opponents | H / A | ResultF – A | Scorers | Attendance | |
|---|---|---|---|---|---|---|---|
| 10 August 1999 | Round 1 First Leg | Darlington | A | 1 – 1 | 5,361 | ||
| 24 August 1999 | Round 1 Second Leg | Darlington | H | 5 – 3 6 – 4 (agg) | Reed 5' (og), Gardner 6', Taylor 50', Frandsen 55', Johansen 71' (pen) | 4,991 | |
| 14 September 1999 | Round 2 First Leg | Gillingham | A | 4 – 1 | Cox 17', Guðjohnsen (2) 44', 58', Bergsson 64' | 4,996 | |
| 21 September 1999 | Round 2 Second Leg | Gillingham | H | 2 – 0 6 – 1 (agg) | Hansen 4', Holdsworth 7' | 3,673 | |
| 13 October 1999 | Round 3 | Derby County | A | 2 – 1 | Fish 45', Johansen 88' | 20,242 | |
| 30 November 1999 | Round 4 | Sheffield Wednesday | H | 1 – 0 | Eliott 53' | 12,543 | |
| 14 December 1999 | Round 5 | Wimbledon | H | 2 – 1 | Guðjohnsen 34', Johansen 39' (pen) | 9,463 | |
| 12 January 2000 | Semi Final First Leg | Tranmere Rovers | H | 0 – 1 | 13,303 | ||
| 26 January 2000 | Semi Final Second Leg | Tranmere Rovers | A | 0 – 3 0 – 4 (agg) | 15,834 |
Bolton used a total of 30 players during the season.
| P | Player | Position | FL | FAC | LC | Total | |
|---|---|---|---|---|---|---|---|
| 1 | Michael Johansen | Midfielder | 47 (1) | 8 (1) | 5 (0) | 60 (1) | |
| 2 | Claus Jensen | Midfielder | 44 (1) | 5 (0) | 6 (0) | 55 (1) | |
| 3 |  Eiður Guðjohnsen | Striker | 41 (1) | 4 (1) | 8 (0) | 53 (2) | |
| 4 | Guðni Bergsson | Defender | 40 (1) | 4 (0) | 7 (0) | 51 (1) | |
| 5 | Mike Whitlow | Defender | 38 (2) | 5 (0) | 7 (0) | 50 (2) | |
| 6 | Mark Fish | Defender | 34 (0) | 4 (0) | 5 (0) | 43 (0) | |
| 7 |  Jussi Jääskeläinen | Goalkeeper | 36 (1) | 3 (0) | 2 (0) | 41 (1) | |
| 8 |  Ricardo Gardner | Midfielder | 27 (3) | 2 (2) | 9 (0) | 38 (5) | |
| 9 | Dean Holdsworth | Striker | 24 (13) | 2 (0) | 3 (2) | 29 (15) | |
| 10 | Robbie Elliott | Defender | 23 (6) | 3 (0) | 3 (1) | 29 (7) | |
| 11 | Bo Hansen | Midfielder/Striker | 16 (15) | 1 (0) | 4 (1) | 21 (16) | |
| 12 | Bob Taylor | Striker | 15 (12) | 3 (1) | 3 (2) | 21 (15) | |
| 13 | Allan Johnston | Midfielder | 19 (2) | 2 (0) | 0 (0) | 21 (2) | |
| 14 | Jimmy Phillips | Defender | 16 (9) | 0 (0) | 3 (1) | 19 (10) | |
| 15 | Paul Warhurst | Defender/Midfielder | 17 (4) | 1 (1) | 1 (3) | 19 (8) | |
| 16 | Paul Ritchie | Midfielder | 15 (1) | 3 (1) | 1 (0) | 19 (2) | |
| 17 | Neil Cox | Defender | 15 (0) | 0 (0) | 4 (0) | 19 (0) | |
| 18 | Andy Todd | Defender | 10 (2) | 0 (0) | 4 (0) | 14 (2) | |
| 19 | Keith Branagan | Goalkeeper | 11 (0) | 0 (0) | 3 (0) | 14 (0) | |
| 20 |  Franck Passi | Midfielder | 7 (9) | 2 (1) | 2 (0) | 11 (10) | |
| 21 | Dean Holden | Defender | 6 (6) | 3 (1) | 2 (1) | 11 (8) | |
| 22 | John O'Kane | Defender | 7 (4) | 1 (1) | 2 (0) | 10 (5) | |
| 23 | Per Frandsen | Midfielder | 7 (0) | 0 (0) | 3 (0) | 10 (0) | |
| 24 | Greg Strong | Defender | 6 (0) | 0 (0) | 3 (1) | 9 (1) | |
| 25 | Gareth Farrelly | Midfielder | 8 (3) | 0 (1) | 0 (0) | 8 (4) | |
| 26 | Steve Banks | Goalkeeper | 2 (0) | 2 (0) | 4 (0) | 8 (0) | |
| 27 | Hasney Aljofree | Striker | 3 (5) | 0 (2) | 3 (2) | 6 (9) | |
| 28 | Darren Holloway | Defender | 3 (1) | 0 (0) | 0 (0) | 3 (1) | |
| 29 | Kevin Nolan | Midfielder | 0 (4) | 0 (0) | 0 (0) | 0 (4) | |
| 30 | Mickael Kaprielian | Midfielder | 0 (1) | 0 (0) | 0 (0) | 0 (1) |
| P | Player | Position | FL | FAC | LC | Total | |
|---|---|---|---|---|---|---|---|
| 1 | Eiður Guðjohnsen | Striker | 14 | 4 | 3 | 21 | |
| 2 | Dean Holdsworth | Striker | 14 | 0 | 1 | 15 | |
| 3 |  Bo Hansen | Midfielder | 9 | 1 | 1 | 11 | |
| 4= | Ricardo Gardner | Midfielder | 5 | 1 | 0 | 6 | |
| 4= | Claus Jensen | Midfielder | 6 | 0 | 0 | 6 | |
| 4= | Michael Johansen | Midfielder | 3 | 0 | 3 | 6 | |
| 4= | Bob Taylor | Striker | 3 | 1 | 2 | 6 |