Jose Mourinho is still haunted by his failure to win the Champions League with Real Madrid.
Los Blancos have lifted the European Cup a record 13 times – but Mourinho did not get his hands on the trophy with the La Liga giants despite reaching the semi-finals for three successive seasons.
Of course, the Tottenham boss has won club football’s biggest prize with Porto and Inter Milan – but his frustration in the competition with Real still rankles with him.
And he remembers one night in particular as the “worst moment” of his managerial career – the penalty shootout defeat to Bayern Munich in the 2011/12 competition.
The previous season – Mourinho’s first in the Madrid hotseat – it had been eventual winners Barcelona who ended their fierce rivals’ Champions League bid.
During Mourinho’s final season in charge, the 2012/13 campaign, his side were denied a place in the final by Borussia Dortmund.
But the 2012 defeat to Bayern sticks out for the 57-year-old, as he believed he had the best team in Europe at the time.
The Bundesliga giants were beaten by Chelsea in the final – and Mourinho reckons he would have led Real to victory over his former side.
“If I have to choose the worst moment, it is that elimination with Madrid,” Mourinho said in an interview with Portuguese television channel Sic reported by Marca.
“We were the best team in Europe, without a doubt, we won La Liga beating all the records for points and goals and we would have won that final, I have no doubts.”
Cristiano Ronaldo had given Madrid control of the tie, scoring twice in the second leg to wipe out Bayern’s 1-0 lead from the opening fixture.
But Arjen Robben equalised to level the tie, while Bastian Schweinsteiger fired home thwe winning penalty in the shootout after Manuel Neuer had saved spot-kicks from Ronaldo and Kaka.
Mourinho said: “And the most cruel for me it is that we chose Cristiano Ronaldo, Kaká and Sergio Ramos for that round.
“They were a guarantee from the penalty spot, and that those who never fail would fail me… “
Mourinho also remembers another galling Champions League semi-final moment – when his Chelsea side were beaten by Liverpool thanks to what the Portuguese manager termed “a ghost goal”.
Three minutes into the 2005 semi-final clash, Garcia fired home to see William Gallas hack his shot off the line.
The goal was awarded, with Liverpool midfielder Garcia later claiming he was confident it had crossed the line as he began celebrating.
And while Chelsea went on to win the Premier League title that season, Garcia’s winner propelled Liverpool on their way towards Champions League glory.
But Mourinho is adamant the goal would not have stood today given today’s goal-line technology.
“It was against Liverpool with a goal that today the VAR would not have conceded,” he recalled. “But Madrid’s hurt more, it was harder.”
The previous season, Mourinho had led Porto to an unlikely Champions League triumph.
And he said it still ranks as the greatest achievement of his career.
“We have lived through very happy moments, but if I have to choose one, I’ll take the Champions League with Porto,” the former Manchester United manager said.
“To win that title with a Portuguese team has a special flavour, and since then no Portuguese team has won it and we don’t know when we will win it again.”