Europe has been his hunting ground but Madrid's poor form has made his task against the English Champions more formidable, writes Andy Mitten.
Champions League: Mourinho's test against Manchester City a special one
"Some things are unforeseeable," said Jose Mourinho, the Real Madrid coach, last week. "There aren't many sports where the best team doesn't win."
Mourinho was talking about the knockout element of cup competitions rather than his side's performance against Sevilla on Saturday night.
Despite beating Barcelona in the domestic Super Cup, the Spanish champions have endured a dreadful start to the league season and sit 11th in the table, eight points behind Barca and with just one win from four games.
"What worries me at the moment is that I don't have a team," said Mourinho after the 1-0 defeat in Andalusia. "My team played well against Barcelona but in no other game have they performed."
He will need a team tonight as Madrid's focus switches to their Champions League Group D opener against Manchester City.
Mourinho will be glad to escape the firestorm of negative opinion surrounding the poor league form to concentrate on another Madrid obsession, winning the decmina - a 10th European Cup.
Madrid's record ninth success came a decade ago and since then Barcelona have triumphed three times.
Mourinho has to shape a winning side against a backdrop of an unhappy star player in Cristiano Ronaldo - a dispute likely to be settled by an improved new contract - a non-scoring striker in Karim Benzema and a defence making basic errors which lead to goals.
Mourinho's job is not yet under pressure, but his players have acknowledged their poor physical form, citing the lack of serious training on the American stage of their pre-season tour as a problem.
They are also furious when their coach is so critical of them after each defeat, with Sergio Ramos saying: "It is strange that after just four games the manager is as unhappy with us as he is and we just cannot get our heads up."
Europe offers a brief respite and Mourinho has improved Madrid before in Europe. When he arrived in 2010, the nine times champions had not got beyond the last 16 stage for five consecutive seasons - an unacceptable record for a club of Madrid's stature.
So poor was Madrid's European form, they were not even a top-eight seeded team in the Champions League draw and thus prone to being drawn in tough groups.
Consecutive semi-final appearances - and defeats to Barcelona and Bayern Munich - now see Madrid as a top eight seed, but they have still been drawn in the toughest group alongside the English champions City, the Dutch champions Ajax and the German champions Borussia Dortmund.
Hopes are that Ronaldo, a forlorn figure against Sevilla, continues to perform well against English teams, especially at the Bernabeu.
Madrid's No 7 will also want to excel against the rivals of his former club Manchester United.
City's underwhelming 1-1 draw at Stoke City on Saturday does not look like a problem in comparison to Madrid's issues.
This is their first ever game at the Bernabeu and all 3,600 tickets for their travelling fans quickly sold out, with the club receiving over 10,000 inquiries.
Roberto Mancini, the City manager, has yet to face a Jose Mourinho side, either with Inter Milan or the Manchester club.
Mancini excelled domestically with three successive scudettos at Inter, but his side underachieved in Europe.
It took Mourinho, his replacement, to improve the Milan side, leading them to Champions League success in 2010.
Under Mancini, City were poor on their Champions League debut last season, losing away to Napoli and Bayern Munich in another tough group. They did not recruit the anticipated big name stars in the summer to boost their Champions League campaign, but their Premier League title-winning squad remains formidable.
City are not expected to win the competition this season, but improve on last term's poor form by reaching the knockout stages.
Doing that from such a tough group which starts away to a team who have won their last six European home games, scoring 24 goals, will be difficult, but if mighty Madrid are at a weak point then it is now.
Follow us @SprtNationalUAE