| Club: | Crewe Alexandra |
| Season: | 1998–99 |
| Manager: | Dario Gradi |
| Chairman: | John Bowler |
| Stadium: | Gresty Road |
| League: | First Division |
| League Result: | 18th |
| Cup2: | FA Cup |
| Cup2 Result: | Third round |
| Cup3: | League Cup |
| Cup3 Result: | Third round |
| League Topscorer: | Little (10) |
| Season Topscorer: | Little (12) |
| Average Attendance: | 5,269 |
| Prevseason: | 1997–98 |
| Nextseason: | 1999–2000 |
During the 1998–99 English football season, Crewe Alexandra F.C. competed in the Football League First Division, their 76th in the English Football League.
In the 1998–99 season, Crewe had a disastrous first half of the campaign which saw them almost midway point at the bottom of the table with just 2 wins from 22 league games and 11 points from safety. Even though they managed to get another couple of wins together; by 20 February, Crewe were still bottom and 11 points from safety with 14 league matches remaining and their First Division status was in severe danger of being lost. From then on against the odds, Crewe went on a superb run of just 3 defeats from their remaining 14 league games, winning 7 of them on their way to completing the great escape, the key result being a 3–1 win against Portsmouth which saved them from the drop.
Crewe Alexandra's score comes first[1]
| Win | Draw | Loss |
| Date | Opponent | Venue | Result | Attendance | Scorers | |
|---|---|---|---|---|---|---|
| 8 August 1998 | Norwich City | A | 1–2 | 15,016 | Rivers | |
| 15 August 1998 | Barnsley | H | 3–1 | 5,289 | Smith (pen), Lightfoot (2) | |
| 22 August 1998 | Bury | A | 0–1 | 5,073 | ||
| 28 August 1998 | Bradford City | H | 2–1 | 5,759 | Lunt, Collins | |
| 31 August 1998 | Sheffield United | A | 1–3 | 15,922 | Jack | |
| 8 September 1998 | Crystal Palace | H | 0–1 | 4,977 | ||
| 12 September 1998 | Stockport County | A | 1–1 | 7,302 | J Wright | |
| 19 September 1998 | Bolton Wanderers | H | 4–4 | 5,744 | Little, Charnock, Rivers, Smith | |
| 26 September 1998 | Bristol City | A | 2–5 | 9,810 | Anthrobus (2) | |
| 29 September 1998 | Grimsby Town | A | 1–1 | 5,024 | Rivers | |
| 3 October 1998 | Wolverhampton Wanderers | H | 0–0 | 5,759 | ||
| 17 October 1998 | Birmingham City | A | 1–3 | 20,087 | Johnson | |
| 20 October 1998 | Port Vale | A | 0–1 | 8,205 | ||
| 24 October 1998 | Tranmere Rovers | H | 1–4 | 5,080 | Little | |
| 31 October 1998 | Oxford United | A | 1–1 | 5,607 | Little | |
| 3 November 1998 | Sunderland | H | 1–4 | 5,361 | Little | |
| 7 November 1998 | Swindon Town | H | 0–2 | 4,489 | ||
| 14 November 1998 | Queens Park Rangers | H | 0–2 | 5,001 | ||
| 21 November 1998 | Watford | A | 2–4 | 9,405 | Jack, Little | |
| 28 November 1998 | Ipswich Town | H | 0–3 | 5,165 | ||
| 5 December 1998 | Portsmouth | A | 0–2 | 9,800 | ||
| 8 December 1998 | West Bromwich Albion | H | 1–1 | 5,007 | Anthrobus | |
| 12 December 1998 | Queens Park Rangers | A | 1–0 | 11,296 | J Wright | |
| 19 December 1998 | Huddersfield Town | H | 1–2 | 5,102 | Jack | |
| 26 December 1998 | Bury | H | 3–1 | 5,333 | Little, Rivers, J Wright | |
| 28 December 1998 | Sunderland | A | 0–2 | 41,433 | ||
| 9 January 1999 | Norwich City | H | 3–2 | 4,782 | Street (2), Rivers | |
| 16 January 1999 | Bradford City | A | 1–4 | 12,595 | Little | |
| 30 January 1999 | Sheffield United | H | 1–2 | 5,243 | Jack | |
| 6 February 1999 | Barnsley | A | 2–2 | 15,377 | Jack (2) | |
| 13 February 1999 | Crystal Palace | A | 1–1 | 14,823 | Walton | |
| 20 February 1999 | Stockport County | H | 0–2 | 5,473 | ||
| 27 February 1999 | Bolton Wanderers | A | 3–1 | 19,437 | Johnson, Jack (2) | |
| 13 March 1999 | Swindon Town | A | 2–1 | 7,434 | Jack, Charnock | |
| 16 March 1999 | Grimsby Town | H | 0–0 | 4,855 | ||
| 20 March 1999 | Oxford United | H | 3–1 | 4,791 | Murphy, Little, Smith (pen) | |
| 26 March 1999 | Tranmere Rovers | A | 0–3 | 9,359 | ||
| 30 March 1999 | Wolverhampton Wanderers | A | 0–3 | 24,197 | ||
| 2 April 1999 | Birmingham City | H | 0–0 | 5,582 | ||
| 5 April 1999 | West Bromwich Albion | A | 5–1 | 12,308 | D Wright, J Wright (2), Johnson, Rivers | |
| 10 April 1999 | Port Vale | H | 0–0 | 5,606 | ||
| 17 April 1999 | Watford | H | 0–1 | 5,461 | ||
| 24 April 1999 | Ipswich Town | A | 2–1 | 20,845 | Rivers, Macauley | |
| 27 April 1999 | Bristol City | H | 1–0 | 5,579 | Johnson | |
| 1 May 1999 | Portsmouth | H | 3–1 | 5,759 | Little (2), Smith | |
| 9 May 1999 | Huddersfield Town | A | 0–0 | 15,105 |
See main article: 1998–99 FA Cup.
| R3 | 2 January 1999 | Oxford United | H | 1–3 | 4,207 | Johnson |
See main article: 1998–99 Football League Cup.
| R1 1st Leg | 11 August 1998 | Oldham Athletic | A | 2–3 | 3,766 | Little (2) | |
| R1 2nd Leg | 18 August 1998 | Oldham Athletic | H | 2–0 (won 4–3 on agg) | 3,428 | Jack (2) | |
| R2 1st Leg | 16 September 1998 | Bristol City | A | 1–1 | 3,082 | Rivers | |
| R2 2nd Leg | 22 September 1998 | Bristol City | H | 2–0 (won 3–1 on agg) | 3,089 | Rivers (2) | |
| R3 | 28 October 1998 | Blackburn Rovers | H | 0–1 | 5,403 |