Which Manager Needs a Trophy Most this Season?

Jose Mourinho

Jose Mourinho is one of the most successful managers in world football, having won 25 major honours at the likes of FC Porto, Chelsea, Inter Milan, Real Madrid and Manchester United, however, despite his incredible CV, the Portuguese manager is arguably under as much pressure and criticism as ever, having gone through the longest phase of his managerial career without a trophy.

Life started well for Mourinho at Tottenham Hotspur, as he managed to get them into the Europa League last campaign, whilst this season they lead the Premier League up until their 2-1 loss at Anfield on 16th December, now, they currently find themselves in eighth position, 14 points behind league leaders Manchester City.

Since then, however, Spurs have made it to the Carabao Cup final against Manchester City, which will take place at Wembley Stadium in April. This could present itself with the best chance Tottenham have had of winning a trophy since they last won this competition against Chelsea in 2008.

The Europa League is also a competition which will become vital to Tottenham later on in the season, as due to their faltering league form since midway through the festive period, this may be their only way of qualifying for next season’s UEFA Champions League.

This season could have eerily similar comparisons to Mourinho’s first at United, where he won the Carabao Cup final against Southampton, as well as the UEFA Europa League final against Ajax, which ultimately saw United qualifying for the Champions League that season, following a sixth-placed in the Premier League.

Ole Gunnar Solskjaer

Manchester United's Ole Gunnar Solskjaer is next on the list of managers that are under pressure to win a trophy. United haven’t won a trophy since they won the 2017 Europa League final under Mourinho, despite making it to four semi-finals in the last 18 months against Sevilla in the Europa, as well as Manchester City twice in the League Cup, and in the FA Cup against Chelsea last campaign.

This four-year spell is Manchester United’s longest trophy drought since 1989, where they failed to win a trophy four seasons in a row, ironically then they also had to watch on as Liverpool took several major honours in and around that period.

The Old Trafford club are one that have become used to success since the 26-year reign of Sir Alex Ferguson at the club, and the Norwegian manager will know that more than anyone else that is the case having scored the goal that sealed United a historic treble in 1999.

A trophy for Solskjaer would further justify and visually show the good progress that his side have made since his first game as manager of the club against Cardiff City back in December 2018, and perhaps this season is one of his better chances to do so, having knocked Liverpool out of the FA Cup in the fourth round, as well as being one of the favourites to win the Europa League this time around, with a much-improved squad than that of last campaign.

If Solskjaer wins a trophy at United this season, then it could ultimately give his players the taste of much-needed success which could drive them on to compete and potentially win more major honours in the near future.

Carlo Ancelotti

Carlo Ancelotti is as experienced as they come as a manager, having started his managerial career back in 1995. However, he currently finds himself in an unfamiliar situation to that which he has found himself in the last two decades, as he currently manages Everton, a team who haven’t won a major trophy since they beat Manchester United in the FA Cup in 1995, before following this up by winning the Community Shield the following campaign against Blackburn Rovers.

At Everton, there is a fairly big rebuild that is going on, as owner Farhad Moshiri is looking to move the club forwards both on and off the pitch, as shown by their plans to move grounds from Goodison Park to Bramley-Moore Dock Stadium.

As a club that doesn’t have any recent heritage of winning trophies, there isn’t much pressure on Ancelotti to deliver this at present, with their priorities lying in qualifying for Europe on a regular basis, whilst adding to the talent which they already have, such as Lucas Digne, Allan, Richarlison, James Rodriguez and Dominic Calvert-Lewin.

For the first time in a long time, it feels as though Everton are moving forwards, rather than sideways and backwards and it must be backed up with a trophy, otherwise, what's the point?

Mikel Arteta

Arsenal manager Mikel Arteta finds himself in a peculiar position, as his side continue to underperform in the Premier League, as the Gunners currently sit in 11th place, having won just nine of their 23 league fixtures.

Ironically, if Arteta didn’t win the FA Cup last season, then he might’ve already been sacked by now, as they haven’t shown any signs of progression this season in terms of winning matches, of which Arsenal are expected to do due to the stature of their club.

One thing that has hampered Arsenal, is the lack of creativity in their squad, due to the likes of Mesut Ozil not being registered in any of their squads for “footballing reasons” prior to his move to Fenerbahce. However, fans of the Gunners will be hoping that January loan signing Martin Odegaard will show the form that he showed at Real Sociedad last campaign, where he managed to get 16 goal contributions in all competitions in 36 appearances.

Due to being knocked out of the League Cup by Manchester City, as well as exiting the FA Cup in the fourth-round having been beaten 1-0 away at Southampton due to an early Gabriel own goal, which was followed by a turgid display from Arteta’s side, the Gunners last hope of silverware is the UEFA Europa League where they face Benfica in the next knockout round.

Europa League success also means Champions League qualification, so perhaps Arteta's name is on the line the most.

Pep Guardiola

Finally, on this list is Manchester City manager Pep Guardiola. The former Barcelona and Bayern Munich coach has enjoyed a trophy-laden spell since making the move to the Etihad Stadium in the summer of 2016.

Since Guardiola’s first season at City, he has won eight pieces of silverware. So far this season, that tally looks like it could be added to, as the Citizens look as though they could be runaway leaders of the Premier League, as they currently sit five points clear of city rivals United with a game in hand, as well as having reached the final of the Carabao Cup final having beaten their neighbours in the semi-finals.

Guardiola’s side go into the Carabao Cup final against Tottenham as favourites, having not lost a tie in that competition since they were beaten by United in the 2016/17 season 1-0 at Old Trafford via a Juan Mata strike.

It would take a huge collapse for City not to win a trophy this campaign, and with them firm favourites to beat Swansea City to advance to the quarter-finals of the FA Cup, as well as facing Borussia Monchengladbach in the Champions League, it would be to nobody’s surprise to see them go far in every competition.

Ultimately the Spaniard’s record at City can’t really be questioned, as he is the club’s most successful ever manager, however, he will be desperate to try and win City their first-ever Champions League, a competition which he hasn’t tasted success in since he was Barcelona manager back in 2011.


The most under pressure managers to win a trophy this season are Solskjaer and Arteta, as United are a club known for winning trophies, and to stare down the barrel of going five seasons without winning one would be disastrous. But the Norwegian’s side have shown a lot of progress in a very short time scale, and the path which the former Molde manager is leading his old club down looks like it could be the right one, but if United are to reach the standard that they aspire to be, then a trophy will need to be won sooner rather than later to breed a winning mentality.

Meanwhile, Arteta is under pressure from much of the Arsenal faithful, as his team has neither played the attractive football which fans of the Gunners crave, or ultimately, brought the right results, and if they do get knocked out of the Europa League and see their league form deteriorate, then there will be more questions than answers over the Spaniard’s capabilities.