After Manchester City’s treble achievement last season, football fans and pundits rushed to compare the iconic teams, making combined elevens to determine which squad was better. Both teams contained top talents that have won multiple Premier League titles, dominating their respective eras.
After winning their fifth league title in six years partnered with an FA Cup triumph, Pep Guardiola has overseen the most feared team in England, a feat replicated on the European stage with their dismantling of Real Madrid, Bayern Munich and Borussia Dortmund.
Manchester United possessed a similar fear factor under Sir Alex Ferguson at the time of their treble, winning their fifth league title in seven years whilst beating Inter Milan, Juventus and Bayern Munich on their way to Champions League glory in 1999.
This Manchester United team of the late 90s is often branded as the best of the Premier League era, containing star names from the fabled Class of 92 like David Beckham, Ryan Giggs, Paul Scholes and the Neville brothers. Blended with the experience of Jaap Stam, Roy Keane, Dwight Yorke, Andrew Cole and more, the Red Devils delivered a historic treble under the expert tutelage of Sir Alex Ferguson.
Manchester City could dominate the 2023/24 season in the same manner as the previous season, but studying United’s follow-up season to the treble shows they could be in for a rocky ride.
The 1999 summer transfer window saw Manchester United make one change with seismic consequences. Peter Schmeichel departed Manchester, with the then 36-year-old leaving English football to join Sporting Lisbon on a free transfer. Mark Bosnich and Massimo Taibi were signed to fill the void left by Schmeichel, a decision that would later hurt Ferguson’s team on the pitch.
Quinton Fortune and Mikaël Silvestre signed for a combined fee of £5.5 million. Fortune and Silvestre were good additions to the team, with both players remaining at the club until the early 00s.
The season began with a Charity Shield match against league rivals Arsenal at Wembley Stadium. The first trophy of the season went to Arsenal, beating United 2-1, with Kanu and Ray Parlour striking for the Gunners.
United brushed this defeat aside with six wins from their opening seven league games, notably beating Arsenal 2-1 at Highbury and Liverpool 3-2 at Old Trafford. A second-half brace from Keane gave United the edge in their second meeting of the season against Arsenal, whilst two own goals from Jamie Carragher and a Cole goal secured the win for the Red Devils against bitter rivals, Liverpool.
Between these league games was a UEFA Super Cup final against Lazio, a game United would lose 1-0 as Marcelo Salas scored the decisive goal. Lazio handed United their second cup final defeat of the season, a bruise on the ego of the club and their achievements of the previous season.
The next few league games would see the champions drop points against much weaker opposition. Draws against Wimbledon and Southampton would be followed up with a 5-0 thumping at the hands of Chelsea at Stamford Bridge. These games highlighted United’s goalkeeping weakness, with Taibi dropping clangers, most notably against Southampton, where Taibi let a tame long-range effort from Matt Le Tissier go under his grasp, trickling into the net. The Italian would make just four appearances, dropped in favour of other options.
October was a tricky month for Ferguson’s side, losing 3-1 against Tottenham Hotspur whilst also being eliminated from the League Cup by Aston Villa in the opening round. However, good league form was maintained from November onwards, going unbeaten for the rest of the year.
During this run the reigning European champions travelled to Japan to play in the Intercontinental Cup final. The game would pit the reigning European champions against the current Copa Libertadores winners, Palmeiras. The attendance was 53,372 as the European champions emerged victorious, winning 1-0 courtesy of a goal from captain Keane.
In terms of Champions League progression, Manchester United were doing well, finishing top of the first group stage and going along steadily in the second group stage, beating the likes of Marseille, Croatia Zagreb and Valencia.
Despite the positive run of form, United still struggled to keep clean sheets. Five clean sheets came in the opening 19 games of the Premier League season, and two from nine cup games.
However, masking the defensive issues was the strike force of Cole and Yorke. The partnership was proving as formidable as the previous season, scoring a combined 28 goals in all competitions before the new year.
With United fighting on many fronts, the whole squad had to be utilised, with Ole Gunnar Solskjær and Teddy Sheringham other striking options who were also delivering goals. Solskjær even managed four goals in one game against Everton in December, a feat Cole also achieved against his former club Newcastle United four months earlier.
The Ballon d’Or ceremony was in December, and with United winning the treble, one of their talents was in with a shout for the award. Unfortunately for Beckham, Rivaldo finished first in the voting as the Englishman came runner-up.
As the new year came in, so did controversy. As European champions, Manchester United travelled to Brazil to play in the FIFA Club World Championships. But, United accepted the offer at the expense of the FA Cup, withdrawing from the competition, sparking national outrage.
This decision had possibly backfired, with United going out at the group stage, being held to a draw by Mexican side Necaxa before losing to Brazilians Vasco da Gama.
By March, Manchester United had booked their place in the Champions League quarter-final, finishing top of their table in the second group phase. Four straight wins against Valencia, Bordeaux (2) and Fiorentina alongside a draw on the final game week secured progression.
United were also sitting top of the Premier League, closing out March with a 4-0 away win at Bradford City, featuring a Paul Scholes volley widely regarded as one of the best goals in Premier League history.
The league title looked to be returning to Old Trafford, but the Champions League was another matter. Despite finishing top of their group, United were dealt a tough hand, drawn to play Real Madrid in the quarter-finals. A goalless draw at the Santiago Bernabéu set up a winner-takes-all affair at Old Trafford.
Real Madrid were 3-0 up inside 52 minutes, with a Keane own-goal and Raúl brace giving Los Blancos the advantage. Beckham’s goal in the 64th minute partnered with a late Scholes penalty meant for a nerve-shredding finale, but Vicente del Bosque’s Spaniards would progress, winning the tournament a month later.
Back to the league, and the dominance continued. Manchester United won each of their last eleven league games, romping to a sixth Premier League title. Notable victories in this superb run include a 7-1 home victory against West Ham United, a thrilling 4-3 contest at Middlesbrough, a 4-0 thumping of Sunderland at Old Trafford and a 3-1 victory against Tottenham coming on the day United were handed the Premier League title in front of their fans.
The Red Devils finished the season on 91 points, 18 clear of closest rivals, Arsenal. It was an emphatic defence of the title, scoring 97 goals in a gunslinger approach, adopted by Ferguson again in his later days as United manager.
Voted into the PFA Team of the Year were four United players; Jaap Stam, David Beckham, Roy Keane and Andrew Cole. Sir Alex Ferguson and Roy Keane were voted as manager and player of the season, capping off an excellent league campaign. Dwight Yorke also finished the season as United’s top goalscorer, netting 24 goals in all competitions.
Manchester United still had a great season despite not winning as many trophies as the year before, marking a time when the red half of Manchester ruled the land.
Manchester City could take notes of this follow-up season from Manchester United. This story is relevant to what we may see next season in the Premier League from City and how they attempt to navigate the challenges such high expectations can bring.
Lessons can be learnt regarding who Guardiola decides to keep and who to let go. In United’s instance, letting go of Peter Schmeichel proved to be a costly mistake. The decision to release Schmeichel was later worked on by Ferguson, attempting to resign the Dane the following season before opting for the younger Fabian Barthez.
A similar situation could unfold at Manchester City with the future of Ilkay Gundogan. A vital part of the City jigsaw and Guardiola’s first signing of his tenure, the importance of Gundogan is undeniable. The experience the German adds partnered with his technical skill will leave a huge gap should Gundogan move elsewhere, as reported by the media.
As proved the case for United, navigating all the cup competitions could be testing. The like-for-like replacements City’s squad possess give them the edge over United, making it more likely that City will win more trophies as opposed to United’s one trophy in their follow-up season.
It will be intriguing to see how Manchester City follow up their treble-winning season and how it compares to Manchester United’s 1999/00 campaign. Manchester United suffered a bit of a treble hangover, with City potentially facing the same scenario. But one guarantee is that both Manchester clubs won’t suffer as bad a hangover as Jack Grealish did after his four-day celebration.
