Manchester United travel to Lisbon on Wednesday night to play Benfica in the Champions League, and for United boss José Mourinho, it will be a return to the club where he was given the chance to show his managerial prowess for the first time.
Mourinho’s spell at Benfica was a brief one, but it was one that showed glimpses of the successful career that he would soon embark on, and it would prove to be a case of what might have been for the Eagles had they kept hold of the Special One.
After assisting Sir Bobby Robson and Louis van Gaal in spells at Porto and Barcelona, Mourinho returned to Portugal in the summer of 2000 as an assistant to Jupp Heynckes. By this stage, the German boss, who had taken over from Graeme Souness the previous season, had alienated a large portion of the Benfica fanbase by transfer listing club icon João Pinto, who would then be released to join crosstown rivals Sporting.

The start to the 2000-01 season sealed Heynckes’ fate. Despite winning two out of the first four Primeira Liga games of the season, a defeat to arch-rivals Porto on the opening weekend and a UEFA Cup first round, first leg defeat to Swedish side Halmstads saw Heynckes sacked in September after being jeered by Benfica fans in his last game in charge against Estrela Amadora, where only two late goals by Pierre van Hooijdonk saved the Eagles from defeat.
And so Mourinho was given the managerial reins by João Vale e Azevedo, who by that point was teetering on the rocks as club president and was up for election in a month’s time. There was little stability at the club, with Vale e Azevedo having run up huge debts and at times, Benfica were unable to pay taxes or players’ wages (which would come back to haunt Vale e Azevedo, who was jailed in April 2002 for embezzlement).
Mourinho set high standards for himself. From day one, he knew those standards could not possibly be met, with the level of disarray the club had found himself in. There is a tale that is recounted in Mourinho’s official biography that gave insight into the club’s problems. One thing that the Special One would often do before matches was to assemble a dossier on the strengths and weakness of opponents, something that he took from his time at Barcelona.
However, when he ordered a detailed scouting report on Boavista for his first match in charge, he was shocked to find that it had only 10 players on the diagrams. “What had I gotten myself into? How is this possible at a big professional club like Benfica?” he told his biographer, Luis Lourenço. He would circumvent the scouting department for the rest of his time in charge.

Despite all those troubles behind the scenes, Mourinho had corrected the ship with right-hand man and former Benfica defender Carlos Mozer. Although he was unable to overturn the deficit to Halmstads in the UEFA Cup (only drawing in the second leg), Benfica’s form in the Primeira Liga was solid, winning six of his first eleven games. Despite this, the Eagles were still in sixth, 10 points behind leaders Porto and five points off second-placed Sporting heading into the derby at the start of December.
That derby would prove to be the high point of Mourinho’s time at Benfica. Benfica thumped their crosstown rivals 3-0 with a Van Hooijdonk penalty and a late double from João Tomás sealing the three points. The derby would also prove to be Mourinho’s last game in charge of the Eagles, for the situation behind the scenes had changed.
Vale e Azevedo had been ousted from the club presidency, replaced by Manuel Vilarinho. Vilarinho had earmarked former Benfica player Toni for the job, and in a game of brinksmanship, Mourinho decided to challenge the incoming president after the rousing derby win: give him a new contract and show faith in his management, or he’d walk.
Vilarinho refused and Mourinho wasn’t bluffing. He and Mozer resigned just two days after the derby, saying: “We thought that the only way to end speculation and the constant threat of being sacked in the event of a bad result was renewing our contracts for another season. The president thought it was better not to accept our request. We understood that decision showed a lack of trust in our work and that we should offer our resignation.”

When he joined Porto two years on and won the UEFA Cup and Champions League in consecutive years, Benfica knew they had let a managerial superstar slip from the grasp. Even Vilarinho himself rued his poor judgement. “If it was today Mourinho would not leave Benfica. [Put me] back then [and] I would do exactly the opposite: I would extend his contract. Only later I realised that one’s personality and pride cannot be put before the interest of the institution we serve.”
And now, after stints at some of the biggest clubs in the world, Mourinho returns to the Luz with United in tow, looking to make his mark felt on one of his early stomping grounds. Despite the nature of his departure, he still had some kind words before this encounter. “They are still our most difficult opponents in this group,” he said.
This is despite Benfica surprisingly losing their first two games against CSKA Moscow and Basel, where they received one of their worst European thrashings of the modern era. United will be confident of a win heading into Wednesday, and Mourinho will once again make Benfica fans ponder the question: what might have happened had he stayed?




