| Club: | Swansea City |
| Season: | 1998–99 |
| Manager: | John Hollins |
| Chairman: | Steve Hamer |
| Stadium: | Vetch Field |
| League: | Third Division |
| League Result: | 7th |
| Cup2: | FA Cup |
| Cup2 Result: | Fourth round |
| Cup3: | League Cup |
| Cup3 Result: | First round |
| Cup4: | Football League Trophy |
| Cup4 Result: | Second round |
| League Topscorer: | Watkin (17) |
| Pattern B1: | _blackarc |
| Leftarm1: | ffffff |
| Body1: | ffffff |
| Rightarm1: | ffffff |
| Shorts1: | ffffff |
| Socks1: | ffffff |
| Prevseason: | 1997–98 |
| Nextseason: | 1999–2000 |
During the 1998–99 English football season, Swansea City A.F.C. competed in the Football League Third Division.
In the summer of 1998, John Hollins was appointed as Swansea manager and things soon started to improve. In the 1998–99 season, the club reached the Third Division play-offs, only to lose in extra time at Scunthorpe United. The season was also notable for a third round FA Cup victory over Premiership opponents West Ham United, whose team included Frank Lampard, Joe Cole, Rio Ferdinand and John Hartson. Swansea thus became the first bottom division team to defeat a Premiership club in the FA Cup since the re-organisation of the league structure in 1992.
See main article: 1998–99 Football League.
Swansea City's score comes first[1]
| Win | Draw | Loss |
| Date | Opponent | Venue | Result | Attendance | Scorers | |
|---|---|---|---|---|---|---|
| 8 August 1998 | Exeter City | H | 2–0 | 5,809 | Thomas, Watkin | |
| 15 August 1998 | Cambridge United | A | 1–2 | 3,074 | Casey | |
| 22 August 1998 | Leyton Orient | H | 1–1 | 4,629 | Bird | |
| 29 August 1998 | Mansfield Town | A | 0–1 | 2,421 | ||
| 31 August 1998 | Scunthorpe United | H | 1–2 | 4,024 | Alsop | |
| 5 September 1998 | Brighton & Hove Albion | A | 0–1 | 2,931 | ||
| 8 September 1998 | Carlisle United | A | 2–1 | 2,816 | Howard, Watkin | |
| 12 September 1998 | Scarborough | H | 2–0 | 3,360 | Watkin (pen), Price | |
| 19 September 1998 | Torquay United | A | 1–1 | 2,527 | Smith | |
| 26 September 1998 | Southend United | H | 3–1 | 3,890 | Alsop, Watkin, Bird | |
| 3 October 1998 | Darlington | A | 2–2 | 3,046 | Watkin, Price | |
| 9 October 1998 | Rotherham United | H | 1–1 | 5,180 | Thomas | |
| 17 October 1998 | Chester City | A | 1–1 | 3,926 | Alsop | |
| 20 October 1998 | Shrewsbury Town | A | 0–1 | 2,328 | ||
| 31 October 1998 | Halifax Town | A | 0–2 | 2,383 | ||
| 7 November 1998 | Peterborough United | H | 0–0 | 3,771 | ||
| 10 November 1998 | Plymouth Argyle | A | 2–1 | 4,517 | Watkin, Alsop | |
| 22 November 1998 | Cardiff City | H | 2–1 | 7,757 | Thomas, Bound | |
| 28 November 1998 | Hartlepool United | A | 2–1 | 2,051 | Alsop (2) | |
| 12 December 1998 | Rochdale | H | 1–1 | 4,010 | Alsop | |
| 19 December 1998 | Hull City | A | 2–0 | 4,280 | Appleby, Watkin | |
| 26 December 1998 | Leyton Orient | A | 1–1 | 5,343 | Alsop | |
| 28 December 1998 | Barnet | H | 2–1 | 6,514 | Smith, Watkin | |
| 9 January 1999 | Exeter City | A | 0–4 | 3,213 | ||
| 30 January 1999 | Barnet | A | 1–0 | 2,259 | Appleby | |
| 5 February 1999 | Brighton & Hove Albion | H | 2–2 | 6,563 | Jones, Watkin | |
| 13 February 1999 | Carlisle United | H | 1–1 | 4,753 | Roberts | |
| 16 February 1999 | Brentford | H | 2–1 | 5,109 | Appleby, Watkin | |
| 20 February 1999 | Scarborough | A | 1–2 | 1,512 | Smith | |
| 23 February 1999 | Mansfield Town | H | 1–0 | 4,361 | Alsop | |
| 27 February 1999 | Torquay United | H | 0–0 | 5,594 | ||
| 6 March 1999 | Southend United | A | 0–2 | 3,713 | ||
| 9 March 1999 | Darlington | H | 2–0 | 4,078 | O'Leary, Watkin | |
| 13 March 1999 | Peterborough United | A | 1–0 | 4,182 | Roberts | |
| 20 March 1999 | Halifax Town | H | 1–2 | 4,974 | Cusack | |
| 23 March 1999 | Scunthorpe United | A | 2–1 | 3,631 | Watkin (2) | |
| 3 April 1999 | Chester City | H | 1–1 | 5,994 | Roberts | |
| 5 April 1999 | Rotherham United | A | 0–1 | 4,257 | ||
| 9 April 1999 | Shrewsbury Town | H | 1–1 | 5,113 | Bound | |
| 13 April 1999 | Hartlepool United | H | 1–0 | 4,429 | Smith | |
| 18 April 1999 | Cardiff City | A | 0–0 | 10,809 | ||
| 24 April 1999 | Plymouth Argyle | H | 2–3 | 5,660 | O'Leary, Jones | |
| 1 May 1999 | Rochdale | A | 3–0 | 1,654 | Price (2), Alsop | |
| 4 May 1999 | Brentford | A | 1–4 | 7,156 | Bird | |
| 6 May 1999 | Cambridge United | H | 2–0 | 6,086 | Watkin (2, 1 pen) | |
| 8 May 1999 | Hull City | H | 2–0 | 9,226 | Watkin (2) |
| SF 1st Leg | 16 May 1999 | Scunthorpe United | H | 1–0 | 7,828 | Bound | |
| SF 2nd Leg | 19 May 1999 | Scunthorpe United | A | 1–3 (lost 2–3 on agg) | 7,089 | Bird |
See main article: 1998–99 FA Cup.
| R1 | 13 November 1998 | Millwall | H | 3–0 | 5,728 | Price, Thomas, Alsop | |
| R2 | 5 December 1998 | Stoke City | H | 1–0 | 7,460 | Appleby | |
| R3 | 2 January 1999 | West Ham United | A | 1-1 | 26,039 | Smith, Dicks | |
| Replay | 13 January 1999 | West Ham United | H | 1–0 | 10,116 | Martin Thomas | |
| R4 | 23 January 1999 | Derby County | H | 0–2 |
See main article: 1998–99 Football League Cup.
| R1 1st Leg | 11 August 1998 | Norwich City | H | 1–1 | 3,803 | Cusack | |
| R1 2nd Leg | 18 August 1998 | Norwich City | A | 0–1 (lost 1–2 on agg) | 13,146 |
See main article: 1998–99 Football League Trophy.
| R1S | 8 December 1998 | Barnet | H | 4–1 | 1,017 | Appleby, Smith, Bird (2) | |
| R2S | 5 January 1999 | Gillingham | H | 0–1 | 5,126 |