Alex Ferguson at the Champions League

Multiple Winners of the Premier League Manager of the Year Awards

Gary Lineker said that football was a simple enough game where “22 men chase a ball for 90 minutes and at the end, the Germans always win.” Well, Germany haven’t been so great in recent years, although they may set that straight at Euro 2024 on home soil, despite indifferent form in the build-up to the tournament.

But a more modern version of the quote might substitute Man City for Germany, with the Cityzens having been the dominant force in the Premier League over the last decade and more. They have work to do yet, but they look set to win their fourth PL title in a row, becoming the first team to achieve that feat. And if they do, there is certainly a very good chance that Pep Guardiola would be named Premier League Manager of the Season.

There are various manager of the year (or season) awards, with the League Managers Association prize being the other major one. Pep could well do the double, but our concern in this piece is on the Premier League Manager of the Season award. If Pep does win in 2023/24, that will be his fifth success, although it is worth noting that he has not landed this honour every time City have won the league.

To win such a prize five times would clearly be an incredible feat and would further cement the Catalonian’s place among the greatest managers in, not just the Premier League, but English football full stop. But would five wins make him the most successful manager ever in terms of this honour? Well, no, not by a long way!

Most PL Manager of the Year Wins

Man United legend, Sir Alex Ferguson, has won this award more times than the three other greatest managers of the Premier League era combined! The brilliant Scot boasts 11 successes, which rather puts Pep’s four (or perhaps five depending on when you read this and how the vote goes) in the shade. Before we examine Fergie’s 11 wins in a little more detail, let’s look at all the bosses to have won the Premier League Manager of the Season award more than once.

Multiple Winners

Rank Wins Manager Club
1 11 Sir Alex Ferguson Man United
2 4 Pep Guardiola Man City
3 (joint) 3 José Mourinho & Arsène Wenger Chelsea & Arsenal, respectively
5 2 Jürgen Klopp Liverpool

Details correct prior to the announcement of the 2023/24 award

Winning the League No Guarantee of Success

In total, the managers of 11 different clubs have won this award. It is also worth noting that on five occasions it was handed to a manager whose team did not win the league. The most recent boss to be honoured in this way was Klopp, in 2021/22, when the Reds amassed 92 points in the league to finish second behind Man City.

However, they famously played in every single game they possibly could have, winning both domestic cups and making the Champions League final. In that competition they were the better side too, but missed out after heroics in the big game from Real Madrid goalkeeper, Thibaut Courtois.

The other managers to win this prize but not the league that season are:

  • Tony Pulis, Crystal Palace, 2013/14
  • Alan Pardew, Newcastle United, 2011/12
  • Harry Redknapp, Tottenham Hotspur, 2009/10
  • George Burley, Ipswich Town, 2000/01

Fergie’s 11 Wins

Sir Alex Ferguson
Sir Alex Ferguson (melis /

Let us forget the rest now, and return to the best, the greatest manager the Premier League has ever seen and will ever see. Some may contest both of those points but we doubt anyone will match Fergie’s longevity, with Klopp’s decision to leave Liverpool indicative of the toll managing at the top level can take.

Guardiola may yet stay at City for another decade or more and if he does, and if his club continue to accrue trophies as they are doing, then perhaps there is a debate to be had. However, those are big ifs, and Fergie’s sustained success, ability to rebuild teams and pragmatism to alter his tactical approach make him the undisputed king for now. Perhaps more than anything, the way in which he was able to overcome the vast spending of the newly rich Roman Abramovich Chelsea, and indeed the Abu Dhabi-era City, are testimony to just how good he was.

1993/94 – Fergie Wins for First Time

The first season of the Premier League came in 1992/93 but this award was only established in the rebranded league’s second term. Had it existed in that first campaign, it is a pretty safe bet to say Fergie would have won it, as he guided the Red Devils to their first top-flight title since 1967.

Nonetheless, he had to wait 12 months, by which time he had helped United defend their title, as well as win the FA Cup. They narrowly missed out on a treble that year too, losing to underdogs Aston Villa in the League Cup final in what was a fantastic season for the club.

United Boss Dominates Rest of Decade

Pep Guardiola
Pep Guardiola (Tsutomu Takasu /

United were so strong in this era and were collecting league titles and other trophies for fun. If Pep does land four titles in a row with Man City that would be some achievement but Fergie’s side were just two points (one in 1994/95 and another single point in 1997/98) from landing a hard-to-believe nine league titles in a row between 1992/93 and 2000/01.

They did win the PL seven times in that period though, as well as three FA Cups (all to complete doubles) and the Champions League (making one of those doubles a treble in 1998/99). That success saw United’s fiery Scottish boss win the PL Manager of the Season accolade in 1995/96, 1996/97, 1998/99 and 1999/2000.

New Millennium, Same Old Story

The 21st century saw uber-rich new owners at Chelsea (in 2003) and Man City (2008) but until Fergie eventually stood down it was business as usual by and large, albeit that United now had to cede the title to other clubs just a little more regularly.

Even so, they continued to accumulate trophies at a staggering rate, with Fergie guiding them to the PL title in 2001, 2003, 2007, 2008, 2009, 2011 and 2013. There were two more FA Cup wins, a trio of League Cup victories in the noughties, and another Champions League title, in 2007/08. All of that silverware helped Fergie earn yet more managerial honours in: 2002/03, 2006/07, 2007/08, 2008/09, 2010/11 and 2012/13. Over to you, Pep!