Since starting out in his first full season as a coach with Porto in the 2002/3 campaign, through spells with Chelsea, Inter Milan and Real, the Portuguese has amassed two Champions League trophies, a UEFA Cup, seven league titles and six national cups.
In what looks increasingly likely to be his last campaign with Real, however, the self-styled 'Special One' could be about to end his three-year reign in Spain with a less than impressive record.
He joined the world's richest club by revenue from Inter in 2010, having led the Italians to an historic treble, culminating in their first European Cup victory in 45 years.
Mourinho's Real won the King's Cup by beating Barca 1-0 after extra time in 2011 and a record-breaking La Liga title in 2012 but a third successive Champions League semi-final exit and Barca's league triumph last weekend have left his third year looking pretty thin.
A Spanish Super Cup victory over Barca back in September is his only silverware to date this season, which he himself dismissed as irrelevant, leaving the much-maligned King's Cup as his last chance to sign off with a flourish.
However, a cup triumph would only paper over the cracks of a disintegrating campaign, with dressing-room divisions coming to the fore since the club's defeat to Borussia Dortmund two weeks ago.
Mourinho's public belittling of popular captain and goalkeeper Iker Casillas and defender Pepe, and his declarations of love towards English football have turned many dyed-in-the-wool Real fans against him.
The looked-down-upon King's Cup was not the title he was brought in to win for them; they wanted a tenth European Cup.
On the pitch, Mourinho's main concern is with the defence where Raphael Varane is out injured, but Sergio Ramos and Marcelo look set to be available again after recovering from their respective problems.
Despite their off-field problems, Real head into the final as the overwhelming favourites as they have not lost a Madrid derby with Atletico since 1999.
Diego Simeone's Atletico have little to lose, having achieved their objective for the season with a third-placed finish in La Liga assuring them of Champions League football again after a three-year absence.
Recent history dictates against Atletico ending their 14-year derby misery.
Only last month a second-string Real side, distracted in the middle of their Champions League semi-final with Dortmund and without Cristiano Ronaldo, still managed to win 2-1 at the Calderon.
"We aren't looking backwards," Atletico's Uruguayan defender Diego Godin told reporters.
"Obviously the statistics of how many times they have beaten us are there...but we are in a good run of form and have the same desire and chances to win as they do."
Atletico have a good record in finals over the last few years, winning the Europa League and the European Super Cup in 2010 and 2012, beating Fulham, Inter Milan, Athletic Bilbao and Chelsea, though they lost the 2010 King's Cup final 2-0 to Sevilla.
Argentine Simeone, who helped Atletico to win their last Cup as a player in 1996, has a full squad to choose from and in Brazilian striker Diego Costa has the tournament's leading scorer with seven goals.
Playing at the home of their neighbours has not proved to be a problem for Atletico in the past. Eight of their nine Cup triumphs have come in the Bernabeu, three of which were against Real Madrid, in 1960, 1961 and 1992.