| Club: | Coventry City |
| Season: | 1999–2000 |
| Manager: | Gordon Strachan |
| Chairman: | Bryan Richardson |
| Stadium: | Highfield Road |
| League: | Premiership |
| League Result: | 14th |
| Cup1: | FA Cup |
| Cup1 Result: | Fourth round |
| Cup2: | League Cup |
| Cup2 Result: | Fourth round |
| League Topscorer: | Keane (12) |
| Season Topscorer: | McAllister (13) |
| Highest Attendance: | 23,098 (vs. Liverpool, 1 April) |
| Lowest Attendance: | 17,685 (vs. Derby County, 21 August) |
| Average Attendance: | 20,786 |
| Pattern La1: | _blueshoulders |
| Pattern B1: | _thinbluesideblueshoulders2 |
| Pattern Ra1: | _blueshoulders |
| Pattern Sh1: | _bluesides |
| Pattern So1: | _bluetop |
| Leftarm1: | 87cefa |
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| Rightarm1: | 87cefa |
| Shorts1: | 87cefa |
| Socks1: | 87cefa |
| Pattern La2: | _blackredshoulders |
| Pattern B2: | _blackredshoulders |
| Pattern Ra2: | _blackredshoulders |
| Pattern So2: | _blacktop |
| Leftarm2: | ffffff |
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| Prevseason: | 1998–99 |
| Nextseason: | 2000–01 |
During the 1999–2000 English football season, Coventry City competed in the FA Premier League (known as the FA Carling Premiership for sponsorship reasons).
Coventry City were one of the Premiership's best-performing sides at home during 1999–2000, achieving 12 victories at the Highfield Road stadium. However, they failed to win a single away game all season, ruining their hopes of getting anywhere near the top five, and they were restricted to 14th place in the final table. 1999–2000 also marked the end of 43-year-old goalkeeper Steve Ogrizovic's illustrious career at the club, and severed their final remaining link with the 1987 FA Cup winning side. Robbie Keane proved a successful signing with 12 goals in 34 league appearances.
See main article: 1999–2000 FA Premier League.
Coventry City's score comes first[1]
| Win | Draw | Loss |
| Date | Opponent | Venue | Result | Attendance | Scorers | |
|---|---|---|---|---|---|---|
| 7 August 1999 | Southampton | H | 0–1 | 19,915 | ||
| 11 August 1999 | Leicester City | A | 0–1 | 19,196 | ||
| 14 August 1999 | Wimbledon | A | 1–1 | 10,635 | McAllister (pen) | |
| 21 August 1999 | Derby County | H | 2–0 | 17,685 | Keane (2) | |
| 25 August 1999 | Manchester United | H | 1–2 | 22,024 | Aloisi | |
| 29 August 1999 | Sunderland | A | 1–1 | 39,427 | Keane | |
| 11 September 1999 | Leeds United | H | 3–4 | 21,532 | McAllister (pen), Aloisi, Chippo | |
| 19 September 1999 | Tottenham Hotspur | A | 2–3 | 35,224 | Keane, Chippo | |
| 25 September 1999 | West Ham United | H | 1–0 | 19,993 | Hadji | |
| 2 October 1999 | Everton | A | 1–1 | 34,839 | McAllister | |
| 16 October 1999 | Newcastle United | H | 4–1 | 23,031 | Palmer, Williams, Keane, Hadji | |
| 23 October 1999 | Sheffield Wednesday | A | 0–0 | 23,296 | ||
| 31 October 1999 | Watford | H | 4–0 | 21,700 | Keane, Froggatt, Hadji, McAllister (pen) | |
| 6 November 1999 | Bradford City | A | 1–1 | 17,587 | McAllister | |
| 22 November 1999 | Aston Villa | H | 2–1 | 20,184 | Roussel, Keane | |
| 27 November 1999 | Leicester City | H | 0–1 | 22,021 | ||
| 4 December 1999 | Southampton | A | 0–0 | 15,168 | ||
| 18 December 1999 | Liverpool | A | 0–2 | 44,024 | ||
| 26 December 1999 | Arsenal | H | 3–2 | 22,757 | McAllister, Hadji, Keane | |
| 4 January 2000 | Chelsea | H | 2–2 | 20,164 | Roussel, Keane | |
| 15 January 2000 | Wimbledon | H | 2–0 | 19,012 | McAllister (pen), Keane | |
| 22 January 2000 | Derby County | A | 0–0 | 28,381 | ||
| 5 February 2000 | Manchester United | A | 2–3 | 61,380 | Roussel (2) | |
| 12 February 2000 | Sunderland | H | 3–2 | 22,101 | Keane, Hadji, Roussel | |
| 19 February 2000 | Middlesbrough | A | 0–2 | 32,798 | ||
| 26 February 2000 | Tottenham Hotspur | H | 0–1 | 23,077 | ||
| 5 March 2000 | Leeds United | A | 0–3 | 38,710 | ||
| 11 March 2000 | Aston Villa | A | 0–1 | 33,177 | ||
| 15 March 2000 | Everton | H | 1–0 | 18,518 | McAllister | |
| 18 March 2000 | Bradford City | H | 4–0 | 19,201 | Roussel, Whelan, Eustace, Zúñiga | |
| 26 March 2000 | Arsenal | A | 0–3 | 38,027 | ||
| 1 April 2000 | Liverpool | H | 0–3 | 23,098 | ||
| 12 April 2000 | Chelsea | A | 1–2 | 32,316 | McAllister | |
| 15 April 2000 | Middlesbrough | H | 2–1 | 19,435 | Ince (own goal), Keane | |
| 22 April 2000 | West Ham United | A | 0–5 | 24,719 | ||
| 29 April 2000 | Newcastle United | A | 0–2 | 36,408 | ||
| 6 May 2000 | Sheffield Wednesday | H | 4–1 | 19,921 | McAllister (2), Zúñiga, Hadji | |
| 14 May 2000 | Watford | A | 0–1 | 18,977 |
See main article: 1999–2000 FA Cup.
| R3 | 11 December 1999 | Norwich City | A | 3–1 | 15,702 | Whelan, Roussel, Eustace | |
| R4 | 8 January 2000 | Burnley | H | 3–0 | 22,774 | Chippo (2), Whelan | |
| R5 | 29 January 2000 | Charlton Athletic | H | 2–3 | 23,400 | Roussel (2) |
See main article: 1999–2000 Football League Cup.
| R2 1st Leg | 14 September 1999 | Tranmere Rovers | A | 1–5 | 6,759 | McAllister | |
| R2 2nd Leg | 22 September 1999 | Tranmere Rovers | H | 3–1 (lost 4–6 on agg) | 12,433 | McAllister, Chippo (2) |
The following players did not appear for the first-team this season.
| Date | Pos. | Name | From | Fee |
|---|---|---|---|---|
| 22 June 1999 | GK | Raffaele Nuzzo | Inter | Free |
| 19 July 1999 | MF | Mustapha Hadji | Deportivo | £4,000,000 |
| 26 July 1999 | FW | Stefano Gioacchini | Venezia | £2,000,000 |
| 31 July 1999 | MF | Runar Normann | Lillestrøm | £1,000,000 |
| 18 August 1999 | FW | Robbie Keane | Wolverhampton Wanderers | £6,000,000 |
| 17 September 1999 | MF | Carlton Palmer | Nottingham Forest | £500,000 |
| 8 December 1999 | DF | Tomas Gustafsson | AIK | £250,000 |
| 16 December 1999 | DF | Richard Spong | IF Brommapojkarna | £80,000 |
| 20 January 2000 | FW | Cedric Roussel | AA Gent | £1,200,000 |
| 21 January 2000 | FW | Ysrael Zúñiga | FBC Melgar | £750,000 |
| 24 February 2000 | DF | Colin Hendry | Rangers | £750,000 |
| Date | Pos. | Name | To | Fee | |
|---|---|---|---|---|---|
| 2 June 1999 | DF | Barry Prenderville | Ayr United | Free | |
| 23 June 1999 | MF | Willie Boland | Cardiff City | Free | |
| 29 June 1999 | DF | Philippe Clement | Club Brugge | £800,000 | |
| 1 July 1999 | GK | Tynan Scope | Bristol City | Free | |
| 1 July 1999 | MF | Martin Devaney | Cheltenham Town | Free | |
| 20 July 1999 | MF | George Boateng | Aston Villa | £4,500,000 | |
| 1 August 1999 | DF | Rob Miller | Cambridge United | Free | |
| 11 August 1999 | FW | Darren Huckerby | Leeds United | £4,000,000 | |
| 12 August 1999 | MF | Trond Egil Soltvedt | Southampton | £300,000 | |
| 16 September 1999 | MF | Sam Shilton | Hartlepool United | Free | |
| 17 November 1999 | GK | Raffaele Nuzzo | Reggina | Free | |
| 23 March 2000 | MF | Paul Hall | Walsall | Free |
Transfers in: £15,450,000
Transfers out: £9,600,000
Total spending: £5,850,000
|-! colspan=14 style=background:#dcdcdc; text-align:center| Goalkeepers|-! colspan=14 style=background:#dcdcdc; text-align:center| Defenders|-! colspan=14 style=background:#dcdcdc; text-align:center| Midfielders|-! colspan=14 style=background:#dcdcdc; text-align:center| Forwards|-! colspan=14 style=background:#dcdcdc; text-align:center| Players transferred or loaned out during the season|-