Antonio Conte not only has to get the better of Jose Mourinho at Wembley on Saturday, he also has to overcome his own personal hoodoo as he looks to record his first cup success as a coach.
Despite having numerous stars at his disposal with Chelsea, Juventus, and, to a lesser extent, Italy, Conte has always come up short in both European and domestic cup competitions. His record shows him to be a league specialist, having won three Scudetti and one Premier League title in the past six years.
As a result, he rightly considers himself among the best managers in the game today, alongside the likes of Pep Guardiola, Mourinho and Jurgen Klopp
However, while his cup record may not be something that damages his reputation as a winner, it will be something that he will want to put to bed as soon as possible. This weekend's FA Cup final against Manchester United would be the perfect place to start.
Looking at Conte's list of honours as a coach, four league titles and no cup wins is a big imbalance, especially when one considers just how dominant his Juve side were domestically, even racking up a record-breaking 102 points in the 2013-14 Serie A season.
Indeed, while the Champions League may be a difficult competition to win – even for sides such as Juve and Chelsea, who rank just below Europe's elite – his record doesn't make for good reading. He has led a team into the tournament three times and has made the quarter-finals only once.
Conte is undoubtedly a manager who focuses on the league, utilising his best players to win a competition of greater merit; one that rewards sustained excellence.
This season, though, has been an unusual one for Conte, who has prioritised certain cup games as it became clear by Christmas that there would be no catching runaway leaders Manchester City at the top of the Premier League table.
La maledizione della Coppa Italia ('The curse of the Coppa Italia') was put forward as an excuse for Conte and his Juve team's inability to complete a domestic double during his three years in Turin – interestingly, Massimiliano Allegri has racked up four in a row since taking over – but they did go in 2012 only to be soundly beaten by a Napoli side that had simply wanted it more.
The next two years saw Conte rest players such as Andrea Pirlo, Paul Pogba, Claudio Marchisio, Carlos Tevez and Gianluigi Buffon in the Coppa Italia, as he chased record-breaking points totals in the league and overdue success in Europe.
Conte came similarly unstuck in the EFL Cup last season, as a Chelsea side without Diego Costa, Eden Hazard or Nemanja Matic were beaten by a mediocre West Ham.
The Blues also struggled through what is now known as the Carabao Cup this season with a second-string side. He switched to his first-choice 11 for the semi-final against Arsenal, in what was again an uncharacteristic move based on his career to date.
Chelsea still fell short in the semi-final and poor finishing, coupled with a tired looking group of players that struggled throughout January, saw them beaten by their London rivals.
A second cup final in two years, therefore, makes the FA Cup the competition that Conte performs best in, outside of the leagues.
He rested players throughout the early rounds of last season, even leaving Eden Hazard and Diego Costa on the bench for the semi-final against Tottenham at Wembley, but he brought back the big guns for the final.
It was all in vain, though, as Chelsea, despite being heavy favourites, lost 2-1 to Arsenal, Conte's bogey team. There were obvious similarities to the 2012 Coppa loss to Napoli, too.
Arsenal looked the more determined, hungrier team against a complacent Chelsea side had been celebrating an unexpected Premier League title win in the weeks before.
The former Italy coach believes he is as good a coach as City boss Guardiola, who has just added the League Cup and the Premier League to his already stellar resume.
The Catalan has had what Conte feels he has never possessed: large and complete squads that have been capable of competing on numerous fronts. Despite this, Conte remains hugely disappointed that his side did not record a double last season, when Arsenal were clearly there for the taking.
“Last season we were in the best condition to win the FA Cup but we missed that chance and it was our fault," he acknowledged. "At that moment we were stronger than them."
Going on league placings, United look stronger than Chelsea going into Saturday's Cup final but Conte will be determined to get one over on his Portuguese counterpart.
Mourinho said "Judas is still number one" as Chelsea knocked Manchester United out of the FA Cup last season in the quarter-finals. His response to being booed at Stamford Bridge was a typically direct barb, a pointed reference to the fact that he remains the manager with the most domestic titles in Chelsea's long history.
Manchester United will likely present a more difficult challenge than Napoli or Arsenal in Conte's finals gone by, in a match that will likely represent his final game in charge of the club. A win in the cup may help his legacy at Stamford Bridge, especially if this match proves to be his last.
History may not be on Conte's side, but he and his players have the chance to change everything over the course of 90 minutes on Saturday evening.