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.
May's victory in the final over Bayern Munich is still fresh in his memory but with the brilliance of Cristiano Ronaldo and pumped-up striker Karim Benzema returning to face his former team, Mourinho's prospects look as good as with Inter last year.
Lyon will not just have recent form against Real on their side at the Stade de Gerland.
Their domestic performances have shown a marked improvement of late with a 4-1 derby win at St Etienne and Friday's 4-0 home thumping of AS Nancy boding well.
"You can see that pressure makes us give the best of ourselves," Puel told reporters.
France playmaker Yoann Gourcuff, bought from Girondins Bordeaux in August as a marquee signing, has finally found his verve after a slow start and Jimmy Briand's bicycle kick goal against Nancy was on a par with Wayne Rooney's recent effort.
The only worries for Lyon are goalkeeper Hugo Lloris's bad cold, although he is expected to return against Real, and striker Lisandro Lopez's hamstring problem which is likely to keep the Argentine out of the game.
"Lisandro is slightly injured, his participation against Real is in doubt." added Puel, who has had a series of run-ins with the forward.
Olympique Lyon: 1-Hugo Lloris; 13-Anthony Reveillere, 3-Cris, 5-Dejan Lovren, 20-Aly Cissokho; 6-Kim Kallstrom, 28-Jeremy Toulalan, 29-Yoann Gourcuff; 11-Michel Bastos, 18-Bafetimbi Gomis, 7-Jimmy Briand
Real Madrid: 1-Iker Casillas; 17-Alvaro Arbeloa, 2-Ricardo Carvalho, 3-Pepe, 4-Sergio Ramos; 14-Xabi Alonso, 24-Sami Khedira; 7-Cristiano Ronaldo, 23-Mesut Ozil, 22-Angel Di Maria; 9-Karim Benzema
Referee: Wolfgang Stark (Germany)