1998/99 Premier League season review
Manchester United won the 1998/99 Premier League on the final day, finishing on 79 points, one ahead of Arsenal and four ahead of Chelsea. They came from behind to beat Tottenham 2-1 at Old Trafford on 16 May, the first part of a treble completed by the FA Cup and, ten days later, the Champions League in Barcelona.
It was one of the tightest title races of the era. Arsenal conceded only 17 league goals, and United and Chelsea lost only three league games each. The Golden Boot was shared three ways, by Jimmy Floyd Hasselbaink, Michael Owen and Dwight Yorke on 18 goals.
You can replay the season here with a £100m squad picked from 343 players across all 20 clubs, or read on for how it unfolded.
The summer after France 98
The season began in the shadow of the World Cup. David Beckham had been sent off against Argentina in the last 16 in Saint-Étienne for kicking out at Diego Simeone, and England went out on penalties. A pub hung an effigy of him, and rival fans gave him a hostile reception when he returned for United.
Arsenal started as Double winners and underlined it by beating Manchester United 3-0 in the Charity Shield on 9 August, with goals from Marc Overmars, Christopher Wreh and Nicolas Anelka. United had already spent heavily in response:
- Jaap Stam arrived from PSV Eindhoven for £10.75m.
- Jesper Blomqvist joined from Parma.
- Dwight Yorke signed from Aston Villa on 20 August for a club-record £12.6m.
Chelsea, under Gianluca Vialli, added Marcel Desailly from AC Milan, Albert Ferrer from Barcelona and Pierluigi Casiraghi from Lazio for a club-record £5.4m. On 28 August they beat Real Madrid 1-0 in the Super Cup, with Gustavo Poyet scoring.
There was change elsewhere too. Liverpool began with Roy Evans and Gérard Houllier as joint managers, Walter Smith replaced Howard Kendall at Everton, and Danny Wilson took over at Sheffield Wednesday. Nottingham Forest, Middlesbrough and Charlton Athletic were promoted, with Charlton playing their first Premier League season.
How United won the league by a point
Chelsea were top over Christmas and into the middle of January. Manchester United lost 3-2 at home to Middlesbrough on 19 December, their only home league defeat of the season.
That defeat turned out to be the last of their season. From a 3-0 win over Nottingham Forest on 26 December, United went 33 games unbeaten in all competitions. On 6 February they won 8-1 at Forest, with Ole Gunnar Solskjær scoring four times in about ten minutes as a substitute. It stood as the Premier League's biggest away win for 20 years. Yorke (18 league goals) and Andy Cole (17) scored 35 between them.
Arsenal were just as relentless. After losing at Aston Villa in December, they went 19 league games unbeaten. Nicolas Anelka scored 17 league goals, including a hat-trick against Leicester, and Nwankwo Kanu arrived from Internazionale in January. Behind them, David Seaman kept 19 clean sheets, and Arsenal conceded only 17 goals all season. A 6-1 win over Middlesbrough in April put them top for the first time.
Chelsea's challenge faded in April, when three draws in a row left them behind. They finished third on 75 points with only three defeats all season, and Gianfranco Zola scored 13 league goals.
The final week
The title turned in the last eight days:
- 11 May: Arsenal lost at Leeds, beaten by a late Jimmy Floyd Hasselbaink goal.
- 12 May: United drew 0-0 at Blackburn, a result that relegated their opponents, now managed by Ferguson's former assistant Brian Kidd.
- 16 May: United went a goal down at home to Tottenham through Les Ferdinand. David Beckham equalised just before half-time and Cole scored three minutes into the second half. United won 2-1, and Arsenal's win over Aston Villa, with a second-half goal from Kanu, left them a point short.
The treble
The league was the first of three trophies in eleven days. The FA Cup run had already produced its own drama. In the semi-final replay against Arsenal on 14 April, Roy Keane was sent off, Peter Schmeichel saved Dennis Bergkamp's injury-time penalty, and Ryan Giggs ran through the Arsenal defence to win it in extra time.
United beat Newcastle 2-0 in the FA Cup final on 22 May, with goals from Teddy Sheringham and Paul Scholes. On 26 May, at the Camp Nou, they trailed Bayern Munich to a sixth-minute Mario Basler free kick until injury time. Sheringham equalised and Solskjær won it in the third minute of stoppage time. Alex Ferguson was knighted that summer.
Leeds, Europe and a season of sackings
The top three took the Champions League places, and Leeds finished a clear fourth on 67 points. George Graham had left for Tottenham early in the season, and under David O'Leary Leeds put together the season's longest winning run, seven games. Hasselbaink's 18 goals earned him a share of the Golden Boot.
The other European places went like this:
- Leeds (4th) took the league's UEFA Cup place.
- Newcastle went into the UEFA Cup as FA Cup runners-up, because United's place came through the Champions League.
- Tottenham qualified by winning the League Cup, beating Leicester 1-0 in the final on 21 March.
- West Ham finished fifth and entered the Intertoto Cup.
Liverpool were seventh. Their joint-management experiment ended on 12 November when Roy Evans resigned, leaving Houllier in sole charge. Owen still scored 18 league goals, and a 7-1 win over Southampton in January was the biggest home win of the season.
It was a season of upheaval in the dugout. Newcastle sacked Kenny Dalglish on 27 August and appointed Ruud Gullit the same day. Tottenham sacked Christian Gross on 5 September before bringing in Graham on 1 October. Blackburn sacked Roy Hodgson in November, Nottingham Forest sacked Dave Bassett on 5 January and turned to Ron Atkinson, and Wimbledon's Joe Kinnear stepped away through illness in March.
The relegation fight
Two of the three promoted clubs went straight back down, along with a former champion:
- Nottingham Forest finished bottom on 30 points and were relegated with three games left, after a 2-0 defeat at Aston Villa on 24 April. They went 19 league games without a win. Pierre van Hooijdonk had refused to return after the summer, feeling let down when Forest sold Kevin Campbell. When he came back, he scored a free kick against Derby and celebrated alone.
- Blackburn, champions only four years earlier, went down in 19th. Their relegation was confirmed by the 0-0 draw with United on 12 May.
- Charlton fell on the final day of their first Premier League season, losing 1-0 at home to Sheffield Wednesday. They also had the season's longest losing run, eight games.
Southampton survived in 17th with 41 points, five clear of Charlton.
1998/99 Premier League final table
| # | Club | P | W | D | L | GF | GA | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|
| 1 | Manchester United | 38 | 22 | 13 | 3 | 80 | 37 | +43 | 79 |
| 2 | Arsenal | 38 | 22 | 12 | 4 | 59 | 17 | +42 | 78 |
| 3 | Chelsea | 38 | 20 | 15 | 3 | 57 | 30 | +27 | 75 |
| 4 | Leeds | 38 | 18 | 13 | 7 | 62 | 34 | +28 | 67 |
| 5 | West Ham | 38 | 16 | 9 | 13 | 46 | 53 | -7 | 57 |
| 6 | Aston Villa | 38 | 15 | 10 | 13 | 51 | 46 | +5 | 55 |
| 7 | Liverpool | 38 | 15 | 9 | 14 | 68 | 49 | +19 | 54 |
| 8 | Derby | 38 | 13 | 13 | 12 | 40 | 45 | -5 | 52 |
| 9 | Middlesbrough | 38 | 12 | 15 | 11 | 48 | 54 | -6 | 51 |
| 10 | Leicester | 38 | 12 | 13 | 13 | 40 | 46 | -6 | 49 |
| 11 | Tottenham Hotspur | 38 | 11 | 14 | 13 | 47 | 50 | -3 | 47 |
| 12 | Sheffield Wednesday | 38 | 13 | 7 | 18 | 41 | 42 | -1 | 46 |
| 13 | Newcastle | 38 | 11 | 13 | 14 | 48 | 54 | -6 | 46 |
| 14 | Everton | 38 | 11 | 10 | 17 | 42 | 47 | -5 | 43 |
| 15 | Coventry | 38 | 11 | 9 | 18 | 39 | 51 | -12 | 42 |
| 16 | Wimbledon | 38 | 10 | 12 | 16 | 40 | 63 | -23 | 42 |
| 17 | Southampton | 38 | 11 | 8 | 19 | 37 | 64 | -27 | 41 |
| 18 | Charlton | 38 | 8 | 12 | 18 | 41 | 56 | -15 | 36 |
| 19 | Blackburn | 38 | 7 | 14 | 17 | 38 | 52 | -14 | 35 |
| 20 | Nottingham Forest | 38 | 7 | 9 | 22 | 35 | 69 | -34 | 30 |
The bottom three were relegated. In the game, every result behind this table plays out as it really happened.
1998/99 top scorers
| Player | Goals | Assists | Our price |
|---|---|---|---|
| Michael Owen Liverpool | 18 | 5 | £8.5m |
| Dwight Yorke Manchester United | 18 | 11 | £11.5m |
| Jimmy Floyd Hasselbaink Leeds | 18 | 13 | £10.5m |
| Andy Cole Manchester United | 17 | 3 | £9.0m |
| Nicolas Anelka Arsenal | 17 | 5 | £9.5m |
| Hámilton Ricard Middlesbrough | 15 | 3 | £7.5m |
| Robbie Fowler Liverpool | 14 | 5 | £8.0m |
| Alan Shearer Newcastle | 14 | 3 | £7.5m |
| Julian Joachim Aston Villa | 14 | 4 | £8.0m |
| Dion Dublin Aston Villa | 14 | 5 | £8.0m |
1998/99 assist leaders
| Player | Assists | Goals | Our price |
|---|---|---|---|
| Dennis Bergkamp Arsenal | 13 | 12 | £10.0m |
| Jimmy Floyd Hasselbaink Leeds | 13 | 18 | £10.5m |
| Dwight Yorke Manchester United | 11 | 18 | £11.5m |
| David Beckham Manchester United | 11 | 6 | £11.5m |
| Steve Guppy Leicester | 11 | 4 | £8.5m |
| Eyal Berkovic West Ham | 10 | 3 | £7.5m |
| David Ginola Tottenham Hotspur | 10 | 3 | £7.0m |
| Darren Anderton Tottenham Hotspur | 9 | 3 | £7.0m |
| Harry Kewell Leeds | 9 | 6 | £10.0m |
| Matt Le Tissier Southampton | 7 | 7 | £7.5m |
League goals and assists only. Players who moved clubs mid-season are listed under the club they played most for.
Surprises and disappointments
Some clubs did far better than expected:
- Middlesbrough came up and finished ninth, their best league position in more than 20 years. Hámilton Ricard scored 15 league goals, and they were the only side to win at Old Trafford in the league.
- David Ginola won both the PFA and the Football Writers' player of the year awards, despite Tottenham finishing 11th.
- West Ham finished fifth despite conceding more league goals than they scored, 53 against 46.
Others had seasons to forget:
- Blackburn went from champions to relegation in four years, despite spending more than £15m on Kevin Davies, Ashley Ward and Jason McAteer. Chris Sutton managed three league goals in 17 appearances.
- Newcastle finished 13th and lost the FA Cup final, in Gullit's first season in charge.
- Arsenal went out of the Champions League in the group stage, playing their home games at Wembley.
- Chelsea's record signing Casiraghi had his season, and his career, ended by a knee injury after scoring once. Brian Laudrup left for Copenhagen after scoring one goal for the club.
The PFA Team of the Year and the season's awards
The players' Team of the Year had five from the champions, three from Arsenal and two from Tottenham.
| Position | Players |
|---|---|
| Goalkeeper | Nigel Martyn (Leeds) |
| Defenders | Gary Neville (Manchester United), Sol Campbell (Tottenham), Jaap Stam (Manchester United), Denis Irwin (Manchester United) |
| Midfielders | David Beckham (Manchester United), Emmanuel Petit (Arsenal), Patrick Vieira (Arsenal), David Ginola (Tottenham) |
| Forwards | Dwight Yorke (Manchester United), Nicolas Anelka (Arsenal) |
The individual awards:
- PFA Players' Player of the Year: David Ginola (Tottenham)
- PFA Young Player of the Year: Nicolas Anelka (Arsenal)
- Football Writers' Footballer of the Year: David Ginola (Tottenham)
- Premier League Player of the Season: Dwight Yorke (Manchester United)
- Premier League Manager of the Season: Alex Ferguson (Manchester United)
- Golden Boot: shared by Hasselbaink (Leeds), Owen (Liverpool) and Yorke (Manchester United), with 18 goals each
Most expensive players by position
The premium picks a £100m budget forces you to choose between in 1998/99.
Goalkeepers
- Ed de Goey£6.0m
- Nigel Martyn£6.0m
- Peter Schmeichel£6.0m
Defenders
- Ian Harte£7.0m
- Dan Petrescu£6.5m
- Michael Ball£6.0m
Midfielders
- David Beckham£11.5m
- Gus Poyet£10.5m
- Harry Kewell£10.0m
Forwards
- Dwight Yorke£11.5m
- Jimmy Floyd Hasselbaink£10.5m
- Dennis Bergkamp£10.0m
1998/99 on Retro Fantasy Football
48 managers have finished a 1998/99 season on our leaderboard (as of October 2026). The best scores so far:
- 2,041 pts
- 2,038 pts
- 2,032 pts
- 2,022 pts
- 2,009 pts
Points follow our scoring rules. Think you can beat them?
1998/99 quick answers
Who won the Premier League in 1998/99? Manchester United, with 79 points, one ahead of Arsenal.
Who was relegated in 1998/99? Charlton Athletic, Blackburn Rovers and Nottingham Forest.
Who was the Premier League top scorer in 1998/99? The Golden Boot was shared by Jimmy Floyd Hasselbaink, Michael Owen and Dwight Yorke, with 18 league goals each.
Who was PFA Player of the Year in 1998/99? David Ginola of Tottenham. Nicolas Anelka was Young Player of the Year.
What did Manchester United win in 1998/99? The treble: the Premier League, the FA Cup and the Champions League.
What was the biggest win of the 1998/99 season? Manchester United's 8-1 win at Nottingham Forest on 6 February 1999.