
| Premiership | 38 | 28 | 7 | 3 | 97 | 45 | Champions | MU | |
| League Cup | 1 | 0 | 0 | 1 | 0 | 3 | 3rd round | Leicester City | |
| UEFA Champions League | 14 | 8 | 3 | 3 | 21 | 11 | Quarter-final | Real Madrid | |
| European Super Cup | 1 | 0 | 0 | 1 | 0 | 1 | Lost | Lazio | |
| Intercontinental Cup | 1 | 1 | 0 | 0 | 1 | 0 | Won | MU | |
| Club World Cup | 3 | 1 | 1 | 1 | 4 | 4 | Group Phase | Corinthians | |
| FA Charity Shield | 1 | 0 | 0 | 1 | 1 | 2 | Lost | Arsenal | |
| All matches | 59 | 38 | 11 | 10 | 124 | 66 |
Clicking on a competition above, filters the matches below:
| 1 | Sun 1 Aug 1999 | FA Charity Shield | MU * | 1 - 2 | Arsenal | Wembley | |
| 2 | Sun 8 Aug 1999 | Premiership | Everton | 1 - 1 | MU | Goodison Park | |
| 3 | Wed 11 Aug 1999 | Premiership | MU | 4 - 0 | Sheffield Wednesday | Old Trafford | |
| 4 | Sat 14 Aug 1999 | Premiership | MU | 2 - 0 | Leeds United | Old Trafford | |
| 5 | Sun 22 Aug 1999 | Premiership | Arsenal | 1 - 2 | MU | Highbury | |
| 6 | Wed 25 Aug 1999 | Premiership | Coventry City | 1 - 2 | MU | Highfield Road | |
| 7 | Fri 27 Aug 1999 | European Super Cup | MU * | 0 - 1 | Lazio | Stade Louis II | |
| 8 | Mon 30 Aug 1999 | Premiership | MU | 5 - 1 | Newcastle United | Old Trafford | |
| 9 | Sat 11 Sep 1999 | Premiership | Liverpool | 2 - 3 | MU | Anfield | |
| 10 | Tue 14 Sep 1999 | UEFA Champions League | MU | 0 - 0 | Croatia Zagreb | Old Trafford | |
| 11 | Sat 18 Sep 1999 | Premiership | MU | 1 - 1 | Wimbledon | Old Trafford | |
| 12 | Wed 22 Sep 1999 | UEFA Champions League | Sturm Graz | 0 - 3 | MU | Schwarzenegger | |
| 13 | Sat 25 Sep 1999 | Premiership | MU | 3 - 3 | Southampton | Old Trafford | |
| 14 | Wed 29 Sep 1999 | UEFA Champions League | MU | 2 - 1 | Olympique Marseille | Old Trafford | |
| 15 | Sun 3 Oct 1999 | Premiership | Chelsea | 5 - 0 | MU | Stamford Bridge | |
| 16 | Wed 13 Oct 1999 | League Cup | Aston Villa | 3 - 0 | MU | Villa Park | |
| 17 | Sat 16 Oct 1999 | Premiership | MU | 4 - 1 | Watford | Old Trafford | |
| 18 | Tue 19 Oct 1999 | UEFA Champions League | Olympique Marseille | 1 - 0 | MU | Stade Velodrome | |
| 19 | Sat 23 Oct 1999 | Premiership | Tottenham Hotspur | 3 - 1 | MU | White Hart Lane | |
| 20 | Wed 27 Oct 1999 | UEFA Champions League | Croatia Zagreb | 1 - 2 | MU | Maksimir Stadium | |
| 21 | Sat 30 Oct 1999 | Premiership | MU | 3 - 0 | Aston Villa | Old Trafford | |
| 22 | Tue 2 Nov 1999 | UEFA Champions League | MU | 2 - 1 | Sturm Graz | Old Trafford | |
| 23 | Sat 6 Nov 1999 | Premiership | MU | 2 - 0 | Leicester City | Old Trafford | |
| 24 | Sat 20 Nov 1999 | Premiership | Derby County | 1 - 2 | MU | Pride Park | |
| 25 | Tue 23 Nov 1999 | UEFA Champions League | Fiorentina | 2 - 0 | MU | Artemio Franchi | |
| 26 | Tue 30 Nov 1999 | Intercontinental Cup | MU * | 1 - 0 | Palmeiras | Olympic Stadium, Tokyo | |
| 27 | Sat 4 Dec 1999 | Premiership | MU | 5 - 1 | Everton | Old Trafford | |
| 28 | Wed 8 Dec 1999 | UEFA Champions League | MU | 3 - 0 | Valencia | Old Trafford | |
| 29 | Sat 18 Dec 1999 | Premiership | West Ham United | 2 - 4 | MU | Upton Park | |
| 30 | Sun 26 Dec 1999 | Premiership | MU | 4 - 0 | Bradford City | Old Trafford | |
| 31 | Tue 28 Dec 1999 | Premiership | Sunderland | 2 - 2 | MU | Stadium of Light | |
| 32 | Thu 6 Jan 2000 | Club World Cup | MU * | 1 - 1 | Rayos del Necaxa | Maracana Stadium | |
| 33 | Sat 8 Jan 2000 | Club World Cup | MU * | 1 - 3 | Vasco da Gama | Maracana Stadium | |
| 34 | Tue 11 Jan 2000 | Club World Cup | MU * | 2 - 0 | South Melbourne | Maracana Stadium | |
| 35 | Mon 24 Jan 2000 | Premiership | MU | 1 - 1 | Arsenal | Old Trafford | |
| 36 | Sat 29 Jan 2000 | Premiership | MU | 1 - 0 | Middlesbrough | Old Trafford | |
| 37 | Wed 2 Feb 2000 | Premiership | Sheffield Wednesday | 0 - 1 | MU | Hillsborough | |
| 38 | Sat 5 Feb 2000 | Premiership | MU | 3 - 2 | Coventry City | Old Trafford | |
| 39 | Sat 12 Feb 2000 | Premiership | Newcastle United | 3 - 0 | MU | St James' Park | |
| 40 | Sun 20 Feb 2000 | Premiership | Leeds United | 0 - 1 | MU | Elland Road | |
| 41 | Sat 26 Feb 2000 | Premiership | Wimbledon | 2 - 2 | MU | Selhurst Park | |
| 42 | Wed 1 Mar 2000 | UEFA Champions League | MU | 2 - 0 | Girondins Bordeaux | Old Trafford | |
| 43 | Sat 4 Mar 2000 | Premiership | MU | 1 - 1 | Liverpool | Old Trafford | |
| 44 | Tue 7 Mar 2000 | UEFA Champions League | Girondins Bordeaux | 1 - 2 | MU | Stade Lescure | |
| 45 | Sat 11 Mar 2000 | Premiership | MU | 3 - 1 | Derby County | Old Trafford | |
| 46 | Wed 15 Mar 2000 | UEFA Champions League | MU | 3 - 1 | Fiorentina | Old Trafford | |
| 47 | Sat 18 Mar 2000 | Premiership | Leicester City | 0 - 2 | MU | Filbert Street | |
| 48 | Tue 21 Mar 2000 | UEFA Champions League | Valencia | 0 - 0 | MU | Mestalla | |
| 49 | Sat 25 Mar 2000 | Premiership | Bradford City | 0 - 4 | MU | Valley Parade | |
| 50 | Sat 1 Apr 2000 | Premiership | MU | 7 - 1 | West Ham United | Old Trafford | |
| 51 | Tue 4 Apr 2000 | UEFA Champions League | Real Madrid | 0 - 0 | MU | Bernabeu Stadium | |
| 52 | Mon 10 Apr 2000 | Premiership | Middlesbrough | 3 - 4 | MU | Riverside Stadium | |
| 53 | Sat 15 Apr 2000 | Premiership | MU | 4 - 0 | Sunderland | Old Trafford | |
| 54 | Wed 19 Apr 2000 | UEFA Champions League | MU | 2 - 3 | Real Madrid | Old Trafford | |
| 55 | Sat 22 Apr 2000 | Premiership | Southampton | 1 - 3 | MU | The Dell | |
| 56 | Mon 24 Apr 2000 | Premiership | MU | 3 - 2 | Chelsea | Old Trafford | |
| 57 | Sat 29 Apr 2000 | Premiership | Watford | 2 - 3 | MU | Vicarage Road | |
| 58 | Sat 6 May 2000 | Premiership | MU | 3 - 1 | Tottenham Hotspur | Old Trafford | |
| 59 | Sun 14 May 2000 | Premiership | Aston Villa | 0 - 1 | MU | Villa Park |
In the matches table above, where MU * (or NH *) appears in the home team column, it indicates a match played at a neutral venue.
Squad(35)
name
sts
sbs
aps
gls
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Manchester United won the Premiership again in the 1999-2000 season. It was their sixth title in eight years. They lost only three games and ended with a record number of points (ninety-one).
The team was largely unchanged from the previous year, except in one notable respect. Peter Schmeichel left the demands of the Premiership to play in Portugal. To many, Schmeichel was the best goalkeeper ever to play for Manchester United, and he proved difficult to replace. Six different goalkeepers were used over the next six seasons. For the 1999-2000 season, Mark Bosnich and Massimo Taibi arrived to join Raimond van der Gouw.
In the Premiership, Manchester United looked comfortable. They won six of their first seven games and all of their last eleven. They won the title with four matches still to play and, in the end, finished eighteen points ahead of Arsenal, who were runners-up. They endured only one major reverse; a 5-0 defeat at Chelsea in October.
Manchester United didn’t participate in the FA Cup in 1999-2000. As winners of the previous season’s UEFA Champions League, they were invited to participate in a FIFA World Club Championship in Brazil in January. The FA wanted them to take part, believing it would help England’s (ultimately failed) bid to host the 2006 World Cup. Being in Brazil in January meant they would miss the fourth round of the FA Cup in England and so it was agreed they should withdraw. It wasn’t a popular decision and Manchester United were accused of being disrespectful to the FA Cup. When they got to Brazil, they didn’t progress beyond the group stage.
In the UEFA Champions League Manchester United reached the quarter-finals, where they were defeated by the eventual winners, Real Madrid. After a goal-less game in Madrid, Manchester United lost 3-2 at Old Trafford.
Roy Keane, Manchester United’s captain, signed a new contract during the season. He also won both the Football Writers’ and the Professional Footballers’ Association’s Players’ Player of the Year awards. He did this despite featuring in one the season’s uglier moments, when he and other Manchester United players chased referee Andy D’Urso around Old Trafford following a contentious decision. There were tensions between Alex Ferguson and David Beckham, after Beckham missed training to look after his family. In the manager’s eyes, Beckham’s life-style was interfering with his football. Alex Ferguson himself announced that he would retire at the end of the 2001-02 season, prompting much speculation about who might succeed him. At the end of the season, Manchester United’s Chief Executive Martin Edwards retired and was replaced by Peter Kenyon.
| 7 - 1 | 01/04/00 vs West Ham | |
| 5 - 1 | 04/12/99 vs Everton | |
| 5 - 1 | 30/08/99 vs Newcastle U | |
| 4 - 0 | 26/12/99 vs Brad City | |
| 4 - 0 | 25/03/00 vs Brad City |
| 0 - 5 | 03/10/99 vs Chelsea | |
| 0 - 3 | 13/10/99 vs Aston Villa | |
| 0 - 3 | 12/02/00 vs Newcastle U | |
| 0 - 2 | 23/11/99 vs Fiorentina | |
| 1 - 3 | 23/10/99 vs Spurs |
| 73,000 | 08/01/00 vs Vasco da Gama | |
| 70,185 | 01/08/99 vs Arsenal | |
| 64,119 | 04/04/00 vs Real Madrid | |
| 61,629 | 06/05/00 vs Spurs | |
| 61,619 | 11/03/00 vs Derby Co |
| 1 | Man Utd | 38 | 28 | 7 | 3 | 97 | 45 | 91 | |
| 2 | Arsenal | 38 | 22 | 7 | 9 | 73 | 43 | 73 | |
| 3 | Leeds Utd | 38 | 21 | 6 | 11 | 58 | 43 | 69 | |
| 4 | Liverpool | 38 | 19 | 10 | 9 | 51 | 30 | 67 | |
| 5 | Chelsea | 38 | 18 | 11 | 9 | 53 | 34 | 65 | |
| 6 | Aston Villa | 38 | 15 | 13 | 10 | 46 | 35 | 58 | |
| 7 | Sunderland | 38 | 16 | 10 | 12 | 57 | 56 | 58 | |
| 8 | Leicester | 38 | 16 | 7 | 15 | 55 | 55 | 55 | |
| 9 | West Ham | 38 | 15 | 10 | 13 | 52 | 53 | 55 | |
| 10 | Spurs | 38 | 15 | 8 | 15 | 57 | 49 | 53 | |
| 11 | Newcastle U | 38 | 14 | 10 | 14 | 63 | 54 | 52 | |
| 12 | M'boro | 38 | 14 | 10 | 14 | 46 | 52 | 52 | |
| 13 | Everton | 38 | 12 | 14 | 12 | 59 | 49 | 50 | |
| 14 | Coventry C | 38 | 12 | 8 | 18 | 47 | 54 | 44 | |
| 15 | S'mpton | 38 | 12 | 8 | 18 | 45 | 62 | 44 | |
| 16 | Derby Co | 38 | 9 | 11 | 18 | 44 | 57 | 38 | |
| 17 | Brad City | 38 | 9 | 9 | 20 | 38 | 68 | 36 | |
| 18 | Wimbledon | 38 | 7 | 12 | 19 | 46 | 74 | 33 | |
| 19 | Sheff Wed | 38 | 8 | 7 | 23 | 38 | 70 | 31 | |
| 20 | Watford | 38 | 6 | 6 | 26 | 35 | 77 | 24 |