After guiding Manchester United to a historic Premier League, FA Cup and UEFA Champions League treble the previous season, the newly knighted Sir Alex Ferguson led his team to a sixth PL title in eight seasons, retaining the trophy by a record 18 points.
In claiming the title, United scored a Premier League-high of 97 goals, in a record season for goals, with 1,060 overall scored.
Few could have predicted United being champions again after a number of challengers strengthened in the summer of 1999, but a run of 11 successive wins at the end of the campaign sealed their defence.
Arsenal, who finished a point adrift of Man Utd in 1998/99, replaced the departure of striker Nicolas Anelka with Thierry Henry. The 1998 FIFA World Cup-winning France forward did not take long to establish himself as one of the Premier League's most lethal strikers. A superb effort at Southampton was one of 17 league goals in his debut season.
Henry could not prevent Man Utd stamping their mark on the title race in the first meeting between the two sides on 22 August 1999. Roy Keane scored both goals in a 2-1 victory for United, who were top of the table after four matches. But an error from Massimo Taibi, the replacement for departed goalkeeper Peter Schmeichel, letting Matt Le Tissier’s tame shot through his legs in Southampton’s 3-3 draw at Old Trafford, led to them being knocked off top spot in September.
United were replaced at the top by an exciting Leeds United side, inspired by Harry Kewell, who went on to win the Professional Footballers' Association Young Player of the Year award, and Michael Bridges, who scored 19 goals in his debut season after joining from Sunderland.
A run of 12 wins from 14 matches took David O'Leary's side to the summit over Christmas, while Man Utd were second and Arsenal were third.
The Gunners were involved in one of the season's classic encounters in October when a hat-trick from Nwankwo Kanu, capped off by a superb strike into the top corner from an acute angle, gave Arsenal a 3-2 win against Chelsea, having been 2-0 down.
Sunderland's Kevin Phillips enjoyed a sensational debut campaign in the top flight. Phillips, who formed a prolific partnership with Niall Quinn, scored 30 goals in the league, earning him the Golden Boot and European Golden Shoe, as the promoted Black Cats finished seventh. One of those goals came in a 2-1 derby win over Newcastle United early in the season. It led to Ruud Gullit becoming the first managerial departure after the Magpies lost five of their first six matches.
Gullit was replaced by former England manager Sir Bobby Robson, who led his side to a comprehensive 8-0 victory over Sheffield Wednesday in his first home match in charge. Alan Shearer, who had been dropped to the bench for the Sunderland defeat, was galvanised under Robson and became the second player to score five goals in one Premier League match. Shearer went on to net 23 league goals in 1999/00 as the revived Magpies finished 11th.
Newcastle were the last team to inflict defeat on Man Utd in the 1999/00 season when they won 3-0 at St James' Park on 12 February. The same day, Frank Lampard sealed a 5-4 victory for
West Ham United against Bradford City, and the Hammers would catch the eye again the following month when Paolo Di Canio scored one of the Premier League's greatest goals. The Italian sweetly connected with Trevor Sinclair's diagonal ball and found the far corner with an exquisite volley against Wimbledon.
Egil Olsen had replaced long-serving Joe Kinnear at WImbledon in the summer but “the Crazy Gang” were relegated for the first time after nine defeats from their last 10 matches.
The day before Di Canio's goal, Paul Scholes scored a thunderous volley from a David Beckham corner as Manchester United cruised to a 4-0 win at Bradford City. Scholes followed that up with a hat-trick in a 7-1 win against West Ham at Old Trafford, and they wrapped up the title in style with an 11-match winning streak.
Arsenal were runners-up for the second successive season, while Leeds were the third team to secure UEFA Champions League qualification after edging ahead of Liverpool. The Reds finished fourth after a shock final-day defeat by Bradford, who clinched safety as a result.
David Wetherall's header sealed the victory at Valley Parade as Bradford stayed up at the expense of Wimbledon, Sheffield Wednesday and Watford. The Hornets’ wins over Liverpool and Chelsea were the highlights of a difficult debut season in the Premier League.