Tottenham turned to Jose Mourinho to try and maintain their status as a Champions League club, but a terrible start to the Premier League season leaves the Portuguese with a mountain to climb either domestically or in Europe.
Mourinho’s appointment was not a universally popular one with the Spurs’ support given his past as a two-time Chelsea manager.
He managed to make the right first impression by securing Tottenham’s first away win in the Premier League since January with a 3-2 victory at West Ham on Saturday that was far more comprehensive that the scoreline suggested.
A vital three points cut the gap between Mourinho’s men and the top four to nine points, but strong starts from Liverpool, Leicester, Manchester City and Chelsea mean one of them will have to falter significantly in the coming months to open the door to Spurs.
The fact that Mourinho’s deal signed last week reportedly contains a £2 million bonus for making the top four is an illustration of how tough a task it will be.
Could winning the Champions League for the first time in the club’s history actually be Spurs’ best way to secure the riches and prestige of Europe’s premier club competition for a fifth consecutive season?
Under Mauricio Pochettino, who was sacked after five-and-a-half years in charge last week, Tottenham improved each year in Europe and last season fell just one hurdle short after a dramatic run to Champions League final.
Despite their dreadful domestic form and a 7-2 thrashing at home to Bayern Munich last month, Pochettino left with his side well-placed to reach the last 16 once more.
Victory over Olympiakos in Mourinho’s home debut on Tuesday will secure their passage into the knockout stages.
“I think we can go and win that match at home and qualify in the Champions League,” said Mourinho, who has a proud record of always qualifying from the Champions League group stages in spells as Porto, Chelsea, Inter Milan, Real Madrid and Manchester United.
Mourinho labelled himself “humble” on his return to management after 11 months out of the game last week, but was quick to point out in his first media briefing that, unlike Tottenham, he had never lost a Champions League final.
He has lifted the trophy twice, with Porto and Inter, but the second of those successes came 10 seasons ago and there are questions over whether he is still the man to deliver Champions League glory.
The 56-year-old has failed to win a single knockout tie in the Champions League over the past five years.
The nadir of that run came when the negative approach that has often characterised Mourinho’s sides came undone for Manchester United against Sevilla in the last 16 of the 2017/18 season.
That style contrasts sharply with the thrilling comebacks away from home that carried Spurs to the final in June as they scored three times in Manchester and Amsterdam.
“Before teams just defended and used the counter-attack, now most of the teams have the courage to play,” said City manager Pep Guardiola, after seeing a fearless Chelsea under Frank Lampard go to the Etihad and have secure more possession than the English champions on Saturday.
“Young managers, they have nothing to lose, go forward and that’s why the football is nice.”
Attack has tended to beat defence in the latter stages in recent years with attack-minded Bayern Munich, Real Madrid, Barcelona and Liverpool the only sides to lift the Champions League in the past seven seasons.
Spurs could not have chosen a more different approach. Now they have to see if Mourinho is still capable of Champions League miracles.