1999/00 Premier League season review

By Craig · Published 29 October 2026

Manchester United won the 1999/00 Premier League with 91 points, 18 clear of Arsenal, a record margin at the time. They lost only three league games, won their last 11 in a row, and scored 97 goals.

The season's other headline belonged to Kevin Phillips. He scored 30 league goals for newly promoted Sunderland and became the first Englishman to win the European Golden Shoe.

You can replay the season here with a £100m squad picked from 341 players across all 20 clubs, or read on for how it unfolded.

Draft a squad from 1999/00

The summer after the treble

United went into the season as treble winners but without Peter Schmeichel. Mark Bosnich was signed as his successor, and Massimo Taibi followed from Venezia for £4.5m in August. The other clubs spent heavily to close the gap:

Arsenal sold Nicolas Anelka to Real Madrid for £23m and signed Thierry Henry for an estimated £11m. They also beat United 2-1 in the Charity Shield.
Chelsea paid Blackburn a club-record £10m for Chris Sutton.
Leeds sold Jimmy Floyd Hasselbaink to Atlético Madrid for £12m and bought Michael Bridges from Sunderland for £5m.
Coventry made Robbie Keane their record signing, paying Wolves £6m.
Newcastle paid Ipswich £6.5m for Kieron Dyer.

Sunderland, Bradford City and Watford came up. At Wimbledon, Joe Kinnear stepped down in June and the Norwegian Egil Olsen took over.

Newcastle's season started badly. On 25 August they lost 2-1 at home to Sunderland, with Phillips and Niall Quinn scoring. Ruud Gullit resigned three days later, and Bobby Robson took over in early September. Within weeks his side beat Sheffield Wednesday 8-0, with Alan Shearer scoring five.

How United won by 18 points

The early signs weren't good for the champions. Taibi made high-profile mistakes and went back to Italy after four games, leaving Bosnich and then Raimond van der Gouw in goal. On 3 October United lost 5-0 at Chelsea, a game in which Sutton scored what would be his only league goal of the season.

In January United didn't play in the FA Cup at all. At the Football Association's request, they withdrew from the competition they had won in May to play in the first FIFA Club World Championship in Brazil, where they went out in the group stage.

It made little difference to the league. From 11 March United won their last 11 league games, the longest winning run of the season, including a 7-1 win over West Ham on 1 April. They sealed the title with a 3-1 win at Southampton on 22 April.

Points: 91, from 28 wins, 7 draws and only 3 defeats.
Goals: 97, with Dwight Yorke scoring 20 in the league and Andy Cole 19.
Creator: David Beckham shared the league lead for assists with Newcastle's Nolberto Solano, on 16.
Captain: Roy Keane was named both PFA Players' Player and Football Writers' Footballer of the Year.

Arsenal finished second on 73 points. Henry scored 17 league goals in his first season in England.

United's only setback came in Europe. As holders, they went out of the Champions League in the quarter-finals, losing 3-2 on aggregate to Real Madrid.

Leeds, Europe and the cups

Leeds finished third under David O'Leary and took the last Champions League place on the final day. Bridges scored 19 league goals in his first season at the club, Harry Kewell was named PFA Young Player of the Year, and Nigel Martyn was the goalkeeper in the PFA Team of the Year.

Their season was overshadowed by tragedy. On the eve of the UEFA Cup semi-final first leg against Galatasaray, two Leeds supporters, Kevin Speight and Christopher Loftus, were killed in Istanbul. Leeds lost the tie 4-2 on aggregate.

The English clubs' results elsewhere:

Arsenal reached the UEFA Cup final in Copenhagen on 17 May, but lost on penalties to Galatasaray after a 0-0 draw.
Chelsea reached the Champions League quarter-finals in their first season in the competition, beating Barcelona 3-1 at Stamford Bridge before going out in the second leg. They then won the FA Cup, beating Aston Villa 1-0 on 20 May in the last final at the old Wembley. Roberto Di Matteo scored after David James dropped the ball from a corner.
Leicester won the League Cup for the second time in four years, beating Tranmere 2-1 at Wembley on 27 February. Matt Elliott scored both goals, and Muzzy Izzet played in midfield.

Aston Villa's run to the FA Cup final owed something to Dion Dublin. He broke his neck against Sheffield Wednesday in December, an injury that could have ended his life, but returned three months later and scored in the semi-final shoot-out against Bolton.

Chelsea also made history on 26 December, when they started a game at Southampton without a single English player, the first English league side to do so. They won 2-1. Their goalkeeper Ed de Goey kept 16 clean sheets, more than any other keeper.

The relegation fight

Only one of the three promoted sides went down:

Watford finished bottom with 24 points, a Premier League record low at the time.
Sheffield Wednesday went down in 19th. They had lost 8-0 at Newcastle in September and sacked Danny Wilson in March.
Wimbledon were relegated on the final day, losing 2-0 at Southampton, after 14 years in the top flight. They lost eight games in a row during the season, and Egil Olsen left on 1 May.

Newly promoted Bradford City survived on the final day by beating Liverpool 1-0 with a David Wetherall goal. That result also cost Liverpool the last Champions League place, which went to Leeds. Southampton stayed up in 15th after replacing Dave Jones with Glenn Hoddle in January.

Stories from 1999/00

Jamie Redknapp, Liverpool's captain and the cream suitsLiverpool captain at 26, a cream suit at Wembley, a winning header against Newcastle off the bench, and years lost to injury.
Shay Given, Newcastle's number one for twelve yearsBeating Barcelona at 21, twelve years in Newcastle's goal, and 134 caps for Ireland, more than any other goalkeeper.
Gary Neville, United's one-club captain and the £5,000 runEight titles at one club, a £5,000 fine for celebrating in front of the Liverpool fans, and a second career explaining the game on Sky.
Jamie Carragher, the Evertonian who never left LiverpoolThe Bootle Evertonian who played 737 games for Liverpool: two own goals against United in one game, and cramp in Istanbul.
Stuart Ripley, Blackburn's title winger turned lawyerBlackburn's first Premier League goal, a title-winning season without a league goal of his own, and a law degree that put him on the FA's disciplinary panel.
David Ginola, the Barnsley goal and Player of the YearBlamed by France, adored on Tyneside, then the solo goal at Barnsley and both Player of the Year awards in the season United won the treble.
Georgi Kinkladze, City's magician and the Southampton goalManchester City built everything around him: two Player of the Year awards, the solo goal against Southampton, and two relegations he couldn't stop.
Paolo Di Canio, the Wimbledon volley and West Ham's maverickHe pushed a referee over in 1998, won a FIFA Fair Play award in 2001, and in between scored the greatest goal the Boleyn Ground ever saw.
Robbie Fowler, the Kop's God and a four-minute hat-trickThe Kop called him God: 128 Premier League goals for Liverpool, a hat-trick in four and a half minutes, and the penalty he told the referee not to give.
Les Ferdinand, Sir Les and the 10,000th Premier League goalSir Les on Tyneside: 25 goals in 1995/96, the season Newcastle let a 12-point lead go, and the Premier League's 10,000th goal six years later.
Nigel Martyn, the first £1m keeper and Leeds' greatestThe first £1 million goalkeeper in British football, 137 Premier League clean sheets, and the only post-Revie player in Leeds' greatest ever team.
Juninho, the Little Fella who cried at Elland RoadThe Little Fella: the league's player of the season in a team that went down, three spells at Middlesbrough and a World Cup in between.
Dwight Yorke, Villa's 17 a season and a treble at UnitedSeventeen goals a season at Villa, the treble and a Golden Boot at United, and a hat-trick inside 22 minutes against Arsenal.
Dion Dublin, a Golden Boot and a broken neckA Golden Boot shared three ways in 1997/98, seven goals in his first three games for Villa, and eight more years with a titanium plate in his neck.
Marc Overmars, the goal at Old Trafford that turned 1998Exactly 100 Premier League games, the winner at Old Trafford that turned the 1998 title race, and the first goal of the FA Cup final that sealed the Double.
Chris Sutton, the corner that cost Arsenal and 18 in 1998Shearer's strike partner in Blackburn's 1994/95 title side, a Golden Boot shared three ways in 1997/98, and the stoppage-time corner at Highbury that had Arsenal players chasing him up the tunnel.
Ed de Goey, 27 clean sheets and the 5-0 over Man UtdSix feet six, four trophies in three seasons, a club-record 27 clean sheets in 1999/2000, and the afternoon Chelsea put five past Manchester United.
Kevin Phillips, 30 goals and a Golden Shoe for SunderlandThirty goals in 1999/00, Sunderland's first season back, the only English winner of the European Golden Shoe for 24 years, and the derby winner that finished Ruud Gullit.
Nick Barmby, across Stanley Park and a derby headerGoals for six clubs, two transfer records in 15 months, the walk across Stanley Park and a header against Everton three months later.
Robbie Keane, the cartwheel and a 4-3 at the LaneIreland's record scorer, 126 Premier League goals, the cartwheel and the pistols, and a hat-trick against Everton in the last game his father saw.
Muzzy Izzet, the Premier League's first Turkish playerThe Premier League's first Turkish player: two League Cups, a World Cup semi-final, and a header at the club that let him go.

1999/00 Premier League final table

#	Club	P	W	D	L	GF	GA	GD	Pts
1	Manchester United	38	28	7	3	97	45	+52	91
2	Arsenal	38	22	7	9	73	43	+30	73
3	Leeds	38	21	6	11	58	43	+15	69
4	Liverpool	38	19	10	9	51	30	+21	67
5	Chelsea	38	18	11	9	53	34	+19	65
6	Aston Villa	38	15	13	10	46	35	+11	58
7	Sunderland	38	16	10	12	57	56	+1	58
8	Leicester	38	16	7	15	55	55	0	55
9	West Ham	38	15	10	13	52	53	-1	55
10	Tottenham Hotspur	38	15	8	15	57	49	+8	53
11	Newcastle	38	14	10	14	63	54	+9	52
12	Middlesbrough	38	14	10	14	46	52	-6	52
13	Everton	38	12	14	12	59	49	+10	50
14	Coventry	38	12	8	18	47	54	-7	44
15	Southampton	38	12	8	18	45	62	-17	44
16	Derby	38	9	11	18	44	57	-13	38
17	Bradford	38	9	9	20	38	68	-30	36
18	Wimbledon	38	7	12	19	46	74	-28	33
19	Sheffield Wednesday	38	8	7	23	38	70	-32	31
20	Watford	38	6	6	26	35	77	-42	24

The bottom three were relegated. In the game, every result behind this table plays out as it really happened.

1999/00 top scorers

Player	Goals	Assists	Our price
Kevin Phillips Sunderland	30	4	£12.0m
Alan Shearer Newcastle	23	7	£10.5m
Dwight Yorke Manchester United	20	3	£10.0m
Andy Cole Manchester United	19	4	£9.0m
Michael Bridges Leeds	19	4	£11.5m
Thierry Henry Arsenal	17	8	£9.0m
Paolo Di Canio West Ham	16	13	£9.5m
Chris Armstrong Tottenham Hotspur	14	1	£7.5m
Niall Quinn Sunderland	14	8	£8.5m
Steffen Iversen Tottenham Hotspur	14	8	£8.5m

1999/00 assist leaders

Player	Assists	Goals	Our price
Nolberto Solano Newcastle	15	3	£7.5m
David Beckham Manchester United	15	6	£10.5m
Paolo Di Canio West Ham	13	16	£9.5m
Ryan Giggs Manchester United	12	6	£10.5m
Dennis Bergkamp Arsenal	9	6	£7.0m
Marc Overmars Arsenal	8	7	£8.0m
Paul Merson Aston Villa	8	5	£7.5m
Thierry Henry Arsenal	8	17	£9.0m
Wim Jonk Sheffield Wednesday	8	3	£6.5m
Niall Quinn Sunderland	8	14	£8.5m

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 and players went well beyond expectations:

Sunderland came up and finished seventh, narrowly missing a UEFA Cup place. Phillips and Quinn, their "little and large" partnership, scored 44 league goals between them, and Phillips was named the Premier League's Player of the Season.
Leeds finished third and reached a European semi-final.
Newcastle recovered under Robson from 19th in August to finish 11th, with Shearer scoring 23 league goals.

Others had seasons to forget:

Chris Sutton cost Chelsea a club-record £10m and scored once in the league.
Massimo Taibi lasted four games in United's goal before returning to Italy.
Wimbledon went down after 14 years in the top flight, in Olsen's only season in charge.
Watford collected only 24 points, then the lowest total in Premier League history.

The PFA Team of the Year and the season's awards

The players' Team of the Year had four from Leeds, as many as the champions, even though Leeds finished 22 points behind United.

Position	Players
Goalkeeper	Nigel Martyn (Leeds)
Defenders	Gary Kelly (Leeds), Jaap Stam (Manchester United), Sami Hyypiä (Liverpool), Ian Harte (Leeds)
Midfielders	David Beckham (Manchester United), Roy Keane (Manchester United), Patrick Vieira (Arsenal), Harry Kewell (Leeds)
Forwards	Andy Cole (Manchester United), Kevin Phillips (Sunderland)

The individual awards:

PFA Players' Player of the Year: Roy Keane (Manchester United)
PFA Young Player of the Year: Harry Kewell (Leeds)
Football Writers' Footballer of the Year: Roy Keane (Manchester United)
Premier League Player of the Season: Kevin Phillips (Sunderland)
Premier League Manager of the Season: Alex Ferguson (Manchester United)
Golden Boot: Kevin Phillips (Sunderland), 30 league goals

Most expensive players by position

The premium picks a £100m budget forces you to choose between in 1999/00.

Goalkeepers

Ed de GoeyChelsea · 0 goals, 0 assists£6.0m
David JamesAston Villa · 0 goals, 0 assists£6.0m
Nigel MartynLeeds · 0 goals, 0 assists£6.0m

Defenders

Ian HarteLeeds · 6 goals, 5 assists£7.0m
Christian ZiegeMiddlesbrough · 6 goals, 6 assists£6.5m
Matt ElliottLeicester · 6 goals, 4 assists£6.0m

Midfielders

Michael BridgesLeeds · 19 goals, 4 assists£11.5m
David BeckhamManchester United · 6 goals, 15 assists£10.5m
Ryan GiggsManchester United · 6 goals, 12 assists£10.5m

Forwards

Kevin PhillipsSunderland · 30 goals, 4 assists£12.0m
Alan ShearerNewcastle · 23 goals, 7 assists£10.5m
Dwight YorkeManchester United · 20 goals, 3 assists£10.0m

1999/00 on Retro Fantasy Football

31 managers have finished a 1999/00 season on our leaderboard (as of October 2026). The best scores so far:

2,082 pts
2,072 pts
2,039 pts
2,032 pts
1,994 pts

Points follow our scoring rules. Think you can beat them?

1999/00 quick answers

Who won the Premier League in 1999/00? Manchester United, with 91 points, 18 ahead of Arsenal.

Who was relegated in 1999/00? Wimbledon, Sheffield Wednesday and Watford.

Who was the Premier League top scorer in 1999/00? Kevin Phillips of Sunderland, with 30 league goals. He also won the European Golden Shoe.

Who was PFA Player of the Year in 1999/00? Roy Keane of Manchester United. Harry Kewell of Leeds was Young Player of the Year.

Why didn't Manchester United play in the 1999/00 FA Cup? At the FA's request, they withdrew to play in the first FIFA Club World Championship in Brazil in January 2000.

What was the biggest win of the 1999/00 season? Newcastle's 8-0 win over Sheffield Wednesday in September 1999, when Alan Shearer scored five.

Draft a squad from 1999/00