Jose Mourinho received another damning blow in what has been a torrid season as Tottenham succumbed to a highly disappointing 3-1 home defeat to Manchester United on Sunday.
The three-time Premier League winner is now the outright favourite among the bookies to be the next top-flight manager to lose their job, with Sportsmail reporting in March that Mourinho will be sacked if Tottenham fail to make the top-four.
Despite Tottenham’s poor form of late, a win over Newcastle at the start of April would have seen them leapfrog Chelsea into the Champions League spots, but a woeful draw saw them lose ground, with the following defeat to United making it an even tougher ask.
It’s a rather drastic drop for Tottenham, who were top of the league halfway through December, having beaten Arsenal, Manchester City and Manchester United, while drawing 0-0 with Chelsea.
Even when Tottenham were top of the league, they received widespread criticism for their negative style of play, which has arguably continued as the season has progressed, just without the results.
With just eight hugely important matches remaining for Tottenham this season, Sportsmail looks at the key fixtures that have defined Mourinho’s disappointing campaign.
Tottenham fell to another disappointing defeat on Sunday as Manchester United won 3-1
Tottenham 3-3 West Ham
West Ham celebrated as Manuel Lanzini’s last-gasp equaliser earned an emphatic comeback
Tottenham fans will have hoped that their side’s inexplicable implosion in a 3-3 draw with West Ham back in October was nothing more than a one off after making a strong start to the season. But that proved not to be the case.
After falling to a disappointing 1-0 home defeat to Everton on the opening day of the season, Tottenham had bounced back well, securing 5-2 and 6-1 wins over Southampton and Manchester United respectively.
They looked on track to claim another momentum-boosting victory as the in-form duo Harry Kane and Son Heung-min put Tottenham 3-0 up before half-time, with Gareth Bale coming on as a substitute after 72 minutes to mark his sentimental return with the three points wrapped up.
What followed was utterly jaw-dropping, as the Hammers pulled two back, before Manuel Lanzini’s 94th-minute wonder strike completed the unlikeliest of comebacks.
The draw not only started a trend of conceding late goals that has cost Tottenham 18 points in total this season, second only to Brighton, but it also shifted Mourinho’s approach entirely.
Where they had previously played on the front-foot, attacking at will, they started to opt for a more defence-centred approach, with Mourinho looking to hold onto his leads, rather than kill the game off.
And for a while, it worked. Tottenham actually went the next seven league games unbeaten and moved to the head of the table. But the emphasis had changed, and while the results were good, the attacking football had swiftly evaporated.
Many pundits predicted that if results dried up, the performances would no longer be tolerated – and they were right.
Liverpool 2-1 Tottenham
Roberto Firmino scored a 90th-minute winner a Liverpool beat Tottenham 2-1 in December
Tottenham’s defeat to Liverpool in December was another defining match in Mourinho’s challenging campaign.
When Tottenham traveled to Anfield, they were top of the league and on a run of seven games undefeated. And while Liverpool were in second and behind only on goal difference, they were coming off a draw with 18th-placed Fulham, and had also lost 7-2 to Aston Villa earlier in the season.
This was Tottenham’s chance to really send out a statement and prove Mourinho had actually installed a winning mentality into his previously somewhat fragile side.
That wasn’t to be the case, however, as in what has become a familiar tale, they conceded in the 90th minute to a Roberto Firmino header, who sealed a 2-1 win for the Premier League champions.
Suddenly, the new-found good feeling around the club had taken a dent. Tottenham lost their following game 2-0 at home to Leicester, before conceding in the 86th minute in a 1-1 draw against Wolves. And from first, the north London club swiftly found themselves in fifth and outside of the top-four.
Tottenham crash out of FA Cup
Bernard scored an extra-time winner as Everton beat Tottenham 5-4 in the FA Cup fifth round
Fast forward to February, and Tottenham had dipped yet further to eighth in the Premier League, though a 2-0 win over West Brom saw them sit just four points off fourth-placed Liverpool with a game in hand.
But crucially, Tottenham had reached the Carabao Cup final with a 2-0 win over Brentford in the semi-finals. They were also through to the knockout stages of the Europe League and faced a mouthwatering FA Cup fifth round tie against Everton.
That was where their first cup run came to an end, however, as Bernard’s extra-time winner saw Everton progress to the quarter-finals with a stunning 5-4 victory.
It was a bizarre performance from Tottenham, who suddenly reverted back to a distinctly attacking approach, while abandoning all defensive caution.
Though suffering disappointing defeats throughout the season, it was the first truly big blow for Tottenham, who appointed Mourinho for the sole purpose of winning trophies.
Arsenal 2-1 Tottenham
Mikel Arteta (left) celebrated as his side beat Mourinho’s Tottenham 2-1 at the Emirates
This was another majorly bitter pill to swallow for Tottenham, who relinquished the opportunity to move three points behind Chelsea in fourth with a game in hand.
After their FA Cup defeat to Everton, the poor results continued to come for Tottenham, who lost 3-0 to Manchester City and 2-1 to West Ham in their following two league games.
But they had seemingly then turned a corner. They won five games on the bounce, largely thanks to a resurgent Gareth Bale, who was finally looking back to his old self. They had progressed to the Europa League last-16 with victory over Wolfsberger, and placed a foot into the last-eight with a 2-0 home win over Dinamo Zagreb.
However, against an Arsenal side who had just drawn to Burnley after consecutive defeats to Leicester and Manchester City, they put in a woeful performance, once again losing despite taking a 1-0 lead.
Erik Lamela was sent off after scoring an outrageous opener, and Tottenham were once again left to rue a lack of an ability to hold onto a lead.
Bale, who was admittedly poor, was hooked before the hour mark, and he’s yet to start a game since.
Tottenham knocked out of Europa League
Tottenham were left in disbelief as Dinamo Zagreb won 3-0 to progress to the last-eight
If the Arsenal defeat was bad, what followed was even worse. In the immediately following game, Tottenham relinquished a 2-0 aggregate lead, losing 3-0 on the night after Mislav Orsic completed an incredible hat-trick in extra-time.
Mourinho reportedly refused to speak to his players after bowing out of the Europa League, a competition the Portuguese holds in high regard.
Having already crashed out of the FA Cup and surrendered all possibility of winning the Premier League, this was another damaging blow for Mourinho, who’s only chance of silverware was now the Carabao Cup.
But while no-one expected Tottenham to win the Premier League, and Everton away is certainly not an easy match, this was a genuinely embarrassing defeat, one that only added to the pain of the north London derby loss.
Tottenham 1-3 Manchester United
Substitute Mason Greenwood made the difference in another huge blow for Mourinho
Finally, we move onto Tottenham’s most recent fixture, in which they once again surrendered a 1-0 lead, this time to Manchester United, who eventually ran out 3-1 winners at the Tottenham Hotspur Stadium.
While losing to United is certainly not the worst result in the world, it was a game they simply had to win, after conceding late once more in their previous outing, a 2-2 draw with Newcastle.
With that in mind, Mourinho’s decision making was certainly questionable – both before and throughout the match. Primarily, the decision to leave Toby Alderweireld out once more – this time with Eric Dier coming back into the team – was simply unfathomable.
And with the score settled at 1-1, Ole Gunnar Solskjaer made an attacking substitution, bringing on Mason Greenwood, while Mourinho took off Giovani Lo Celso for Moussa Sissoko.
Their most creative player, Tanguy Ndomeble, was replaced by Erik Lamela on 78 minutes, with Tottenham conceding just a minute later, before Gareth Bale was finally introduced with eight minutes to play.
It was a game Tottenham needed to win, and the substitions just didn’t reflect that.
Carabao Cup final: a chance for redemption
Manchester City beat Tottenham 3-0 when they last played at the Etihad in February
Now, this all sounds a bit doom and gloom, and that is perhaps the feeling around Tottenham at the moment.
However, in the Carabao Cup, Tottenham have the chance to turn their season around. They play Manchester City in the final on April 25, and a win would certainly change the tone on an otherwise troublesome season.
And should Tottenham go on a run and clinch a top-four place, while winning the cup, the season would have to go down as a success.
However, should neither of those scenarios occur, then it’s difficult to see a future for Mourinho at Tottenham.