Jose Mourinho ended Chelsea's half a century wait for an English title, he brought European Cup glory back to Inter Milan after 45 years and now he battles Olympique Lyon's mesmeric hold over mighty Real Madrid.
If there was ever a man to conquer a hoodoo it is the Portuguese coach but he has more than one jinx to deal with in Tuesday's Champions League last-16 first leg in France.Lyon have beaten Real at home three times in a row in the competition including last year where they condemned the Spaniards to their sixth successive last 16 elimination.
Overcoming Claude Puel's team and the mental block of quarter-final progress will be no mean feat but Mourinho, as ever, oozes the confidence that prompted the nine-times winners to appoint him last May.
"No one keeps me awake, neither Lyon nor anyone else," the outspoken Mourinho told reporters after Saturday's comfortable 2-0 La Liga win at home to Levante where he rested several players. "The night I don't sleep well is after the match. Ever since we drew Lyon we have been following them. (Real consultant Zinedine) Zidane knows them and has been giving me information."
On a personal note, Mourinho is bidding to become the first coach to win the Champions League with three different clubs after stunning the European game with Porto's 2004 triumph and then taking just two seasons to mould a winning side at Inter.
Faltering Chelsea visit Copenhagen
The one positive from Chelsea's FA Cup defeat by Everton on penalties is that Carlo Ancelotti's faltering side can now focus solely on the trophy that has proved agonisingly elusive in recent years.
Not that FC Copenhagen will be concerned with that when the Danes host the EPL champions in their atmospheric Parken Stadium on Tuesday in the first leg of their Champions League, last 16 tie.
While there is a huge difference in experience between the two with Copenhagen in uncharted territory up against a club with five Champions League semi-finals in the last seven years, Chelsea's current malaise suggests Ancelotti's side could be in for a testing night in the Danish capital.
Copenhagen have been thorny opponents for some of Europe's big names in recent years. They were undefeated at home in Group D this season, holding Barcelona to a 1-1 draw, while they also enjoyed a victory over Manchester United a few seasons ago.
With Chelsea's Premier League title hopes all but gone and defeat by Everton ending their dream of a third consecutive FA Cup, Ancelotti is now under pressure to deliver Europe's biggest club prize for the first time.
"We wanted to repeat our FA Cup success," the Italian said after penalty misses by Ashley Cole and Nicolas Anelka cost them dear at Stamford Bridge on Saturday.
"It is a very important competition for us, but now we have to move forward and use these days to recover energy and prepare for the next games.
"It is not an easy moment because we have to play very important games but sometimes it is good to play tough games because you are more in focus, so we don't have be afraid to play against Copenhagen, it could be a motivation."
Copenhagen are coached by enigmatic Norwegian Stale Solbakken, who played in midfield for the club before his career was abruptly ended by a heart attack on the training ground.
While Chelsea's season has hit the skids during the English winter, Copenhagen have been on their mid-season break and have not played a competitive fixture since early December.
They have kept sharp by playing in Spain but a battle-hardened Chelsea with a point to prove and 50 million- pound ($81.27 million) striker Fernando Torres eager to justify his huge fee will be an entirely more taxing challenge.