Man United's failure in the FIFA Club World Championship, was surprisingly compounded by the press even more when David Beckham's wife Victoria, admitted on The Big Breakfast that he enjoys wearing her thongs.
Sunderland made an impressive Premiership comeback by finishing seventh and just missing out on a UEFA Cup place, in part due to 30 goals from prolific striker Kevin Phillips.
It also meant that Wimbledon's 14-year spell in the top flight was over and they were relegated to Division One 12 years to the day that they had beaten Liverpool to achieve a shock FA Cup triumph.
Steve Coppell ended his fourth spell as Crystal Palace manager after doing wonders to keep a virtually bankrupt club clear of the Division One relegation zone.
West Bromwich Albion just missed out on the drop zone thanks to a late turn-around in form during the final weeks of the season which followed the appointment of Gary Megson as manager.
David Moyes, 37, showed promise as one of the league's most highly rated young managers after he guided Preston North End to the Division Two championship.
Narrowly avoiding the drop were Oxford United, who struggled all season long despite the club's financial crisis being eased by the arrival of new Tanzanian chairman Firoz Kassam.
Chester City were relegated on the last day of the season, ending their 69-year league career while Shrewsbury Town and Carlisle United saved themselves from Conference football.
Roy Keane was voted Player of the Year by both the PFA and FWA and Dwight Yorke finished as the club's top scorer with 20 Premiership goals.
Martin O'Neill guided Leicester City to their second League Cup triumph in four seasons before moving north of the border to Celtic, whose 'dream team' partnership of Director of Football Kenny Dalglish and Head Coach John Barnes had ended a nightmare as they finished 21 points behind champions Rangers in the SPL title race and had suffered a shock SFA Cup exit at the hands of Inverness Caledonian Thistle, which had inspired The Sun newspaper headline: "Super Caley Go Ballistic, Celtic Are Atrocious".
Leeds United's 22-year-old Australian midfielder Harry Kewell was voted PFA Young Player of the Year after helping to secure a Champions League place for his side.
Kevin Phillips scored 30 Premiership goals for Sunderland to win the Premier League Golden Boot and making him the season's highest scorer among all four English professional divisions.
Liverpool's fourth-place finish meant that they had to settle for a UEFA Cup place, a shock defeat to Bradford City (who defied all the odds to avoid relegation in their first top-flight season for nearly 80 years) preventing them from qualifying for the Champions League on the final day.
Ipswich Town finished in the play-offs for the fourth season in a row, but this time they were successful as they triumphed over Barnsley at Wembley and won promotion back to the Premier League after a five-year absence.
Wolves narrowly missed out on the playoffs for the third season running, while Huddersfield Town's eighth-place finish was perhaps the closest they had come to returning to the top flight since losing their top-flight place in 1972.
Fulham finished ninth as their recent revival continued, but a failure to win a second successive promotion saw Paul Bracewell sacked as manager and replaced with Jean Tigana, who had won a French league title and reached a European Cup semi-final with AS Monaco.
Chesterfield started the season well enough, but a dreadful run of 2 wins in 20 games mid-season consigned them to relegation and spelled the end as manager for John Duncan after seven years.
Oxford United finished one point clear of a second successive relegation, their future secured after being taken over by hotelier Firoz Kassam, who enabled construction work to resume on the club's long-awaited new stadium.
Leading goalscorer: Andy Payton (Burnley) – 27 Swansea and Rotherham, both of whom had been dumped out in the play-off semi-finals the previous year, led the table for virtually the entire season.
In the end, Chester, who had spent virtually the entire season rooted to the bottom of the table and only had the chance of a last-day escape because of similarly poor campaigns by Carlisle and Shrewsbury, were relegated to the Conference.
30 June 1999 – Bradford City prepare for their first time top division season for nearly 80 years with a club record £1.4 million move for Leeds United defender David Wetherall.
24 October 1999 – A Premier League thriller at Goodison Park sees Everton and Leeds United draw 4–4, a result that ends the Yorkshire club's 10-match winning streak.
Elsewhere, a late Trevor Sinclair equalizer for West Ham United stops ten-man Sunderland's ascension to the top; the Black Cats instead rise to third.
Sheffield Wednesday and Watford continue to prop up the rest of the Premier League, accompanied in the drop zone by a Derby County side who had spent the previous two seasons chasing a place in Europe.
30 January 2000 – Blackpool striker Martin Aldridge, 25, on loan to Rushden & Diamonds, dies in an Oxford hospital after being injured in a car crash in Northamptonshire.
Danny Wilson is named FA Premier League Manager of the Month, but the club are still in the relegation zone, though no longer in the bottom place (now occupied by Watford.
[18] 4 March 2000 – Debutant striker Stan Collymore scores a hat-trick for Leicester City in their 5–2 win over Sunderland in the Premier League, just days after his transfer from Aston Villa.
At the other end of the table, Sheffield Wednesday and Watford are looking doomed, with Bradford City occupying the final relegation position and Derby County hovering dangerously close to the drop zone.
2 June 2000 – Chelsea equal the national transfer record (set by Alan Shearer four years ago) with a £15 million move for Jimmy Floyd Hasselbaink.
14 June 2000 – Match of the Day, the longest-running and most popular football programme on British television, is set to end after next season as a result of ITV's £183 million deal to show highlights from Premier League games.