| Club: | Coventry City |
| Season: | 1998–99 |
| Manager: | Gordon Strachan |
| Chairman: | Bryan Richardson |
| Stadium: | Highfield Road |
| League: | Premiership |
| League Result: | 15th |
| Cup2: | FA Cup |
| Cup2 Result: | Fifth round |
| Cup3: | League Cup |
| Cup3 Result: | Third round |
| League Topscorer: | Whelan (10) |
| Season Topscorer: | Whelan (13) |
| Highest Attendance: | 23,098 (vs. Tottenham Hotspur, 26 December) |
| Lowest Attendance: | 6,631 (vs. Southend United, 16 September) |
| Average Attendance: | 20,773 |
| Prevseason: | 1997–98 |
| Nextseason: | 1999–2000 |
During the 1998–99 English football season, Coventry City competed in the FA Premier League.
Coventry City finished 15th in the Premiership – four places lower than last season – but were never in any real danger of being relegated, despite the loss of key striker Dion Dublin to local rivals Aston Villa.[1]
The biggest news of Coventry's season was the announcement of a move to a new 45,000-seat stadium at Foleshill, which was anticipated to be ready by 2002. Manager Gordon Strachan then signed Moroccan international football star Mustapha Hadji, knowing that it would be important to have a top quality team to match the forthcoming new home.[2]
See main article: 1998–99 FA Premier League.
Coventry City's score comes first[3]
| Win | Draw | Loss |
| Date | Opponent | Venue | Result | Attendance | Scorers | |
|---|---|---|---|---|---|---|
| 15 August 1998 | Chelsea | H | 2–1 | 23,042 | Huckerby, Dublin | |
| 22 August 1998 | Nottingham Forest | A | 0–1 | 22,546 | ||
| 29 August 1998 | West Ham United | H | 0–0 | 20,818 | ||
| 9 September 1998 | Liverpool | A | 0–2 | 41,771 | ||
| 12 September 1998 | Manchester United | A | 0–2 | 55,193 | ||
| 19 September 1998 | Newcastle United | H | 1–5 | 22,656 | Whelan | |
| 26 September 1998 | Charlton Athletic | A | 1–1 | 20,043 | Whelan | |
| 3 October 1998 | Aston Villa | H | 1–2 | 22,654 | Soltvedt | |
| 18 October 1998 | Sheffield Wednesday | H | 1–0 | 16,006 | Dublin | |
| 24 October 1998 | Southampton | A | 1–2 | 15,152 | Dublin | |
| 31 October 1998 | Arsenal | H | 0–1 | 23,040 | ||
| 7 November 1998 | Blackburn Rovers | A | 2–1 | 23,779 | Huckerby, Whelan | |
| 15 November 1998 | Everton | H | 3–0 | 19,290 | Froggatt, Huckerby, Whelan | |
| 21 November 1998 | Middlesbrough | A | 0–2 | 34,293 | ||
| 28 November 1998 | Leicester City | H | 1–1 | 19,894 | Huckerby | |
| 5 December 1998 | Wimbledon | A | 1–2 | 11,717 | McAllister (pen) | |
| 14 December 1998 | Leeds United | A | 0–2 | 31,802 | ||
| 19 December 1998 | Derby County | H | 1–1 | 16,627 | Whelan | |
| 26 December 1998 | Tottenham Hotspur | H | 1–1 | 23,098 | Aloisi | |
| 28 December 1998 | West Ham United | A | 0–2 | 25,662 | ||
| 9 January 1999 | Nottingham Forest | H | 4–0 | 17,172 | Huckerby (3), Telfer | |
| 16 January 1999 | Chelsea | A | 1–2 | 34,869 | Huckerby | |
| 30 January 1999 | Liverpool | H | 2–1 | 23,056 | Boateng, Whelan | |
| 6 February 1999 | Tottenham Hotspur | A | 0–0 | 34,376 | ||
| 17 February 1999 | Newcastle United | A | 1–4 | 36,352 | Whelan | |
| 20 February 1999 | Manchester United | H | 0–1 | 22,596 | ||
| 27 February 1999 | Aston Villa | A | 4–1 | 38,799 | Aloisi (2), Boateng (2) | |
| 6 March 1999 | Charlton Athletic | H | 2–1 | 20,259 | Whelan, Soltvedt | |
| 13 March 1999 | Blackburn Rovers | H | 1–1 | 19,701 | Aloisi | |
| 20 March 1999 | Arsenal | A | 0–2 | 38,073 | ||
| 3 April 1999 | Sheffield Wednesday | A | 2–1 | 28,136 | McAllister (pen), Whelan | |
| 5 April 1999 | Southampton | H | 1–0 | 21,402 | Boateng | |
| 11 April 1999 | Everton | A | 0–2 | 32,341 | ||
| 17 April 1999 | Middlesbrough | H | 1–2 | 19,231 | McAllister | |
| 24 April 1999 | Leicester City | A | 0–1 | 20,224 | ||
| 1 May 1999 | Wimbledon | H | 2–1 | 21,200 | Huckerby, Whelan | |
| 8 May 1999 | Derby County | A | 0–0 | 32,450 | ||
| 16 May 1999 | Leeds United | H | 2–2 | 23,049 | Aloisi, Telfer |
See main article: 1998–99 FA Cup.
| R3 | 2 January 1999 | Macclesfield Town | H | 7–0 | 14,197 | Froggatt, Whelan, Payne (own goal), Huckerby (3), Boateng | |
| R4 | 23 January 1999 | Leicester City | A | 3–0 | 21,207 | Whelan, Froggatt, Telfer | |
| R5 | 13 February 1999 | Everton | A | 1–2 | 33,907 | McAllister |
See main article: 1998–99 Football League Cup.
| R2 1st Leg | 16 September 1998 | Southend United | H | 1–0 | 6,631 | Hall | |
| R2 2nd Leg | 22 September 1998 | Southend United | A | 4–0 (won 5–0 on agg) | 6,292 | Boateng, Dublin, Whelan, Soltvedt | |
| R3 | 27 October 1998 | Luton Town | A | 0–2 | 9,051 |
| Date | Pos. | Name | From | Fee | |
|---|---|---|---|---|---|
| 4 June 1998 | DF |  Jean-Guy Wallemme | RC Lens | Undisclosed | |
| 1 August 1998 | DF | Robert Jarni |  Real Betis | £2,600,000 | |
| 7 August 1998 | FW |  Paul Hall | Portsmouth | £300,000 | |
| 26 August 1998 | DF | Marc Edworthy | Crystal Palace | £1,200,000 | |
| 1 October 1998 | MF | Steve Froggatt | Wolverhampton Wanderers | £1,900,000 | |
| 12 October 1998 | MF |  Laurent Delorge | Gent | £1,250,000 | |
| 17 December 1998 | FW |  John Aloisi | Portsmouth | £650,000 | |
| 30 December 1998 | GK | Morten Hyldgaard | Ikast FS | £200,000 | |
| 13 January 1999 | DF |  Muhamed Konjić | AS Monaco | £2,000,000 | |
| 28 May 1999 | MF |  Youssef Chippo | Porto | £1,200,000 |
| Date | Pos. | Name | To | Fee | |
|---|---|---|---|---|---|
| 8 July 1998 | MF | John Salako | Fulham | Free transfer | |
| 16 July 1998 | FW | Viorel Moldovan |  Fenerbahçe | £4,000,000 | |
| 15 August 1998 | DF | Robert Jarni | Real Madrid | £3,400,000 | |
| 2 October 1998 | FW | Simon Haworth | Wigan Athletic | £600,000 | |
| 5 November 1998 | FW | Dion Dublin | Aston Villa | £5,750,000 | |
| 30 December 1998 | DF | Jean-Guy Wallemme | Sochaux | £400,000 |
Transfers in: £11,300,000
Transfers out: £14,150,000
Total spending: £2,850,000
|-! 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 who left the club during the season|-|}