When Chelsea and Tottenham face off in the Premier League this Saturday, different fans' minds will go to different places as they think about players and managers associated with the two clubs. On the pitch, that could mean players like Carlo Cudicini or Conor Gallagher, while manager-wise it could mean Jose Mourinho or Mauricio Pochettino.

Mourinho spent two different spells at Chelsea, winning the Premier League in both stints. However, his time in charge of Spurs was much less successful.

The Portuguese boss took charge in North London during the 2019/20 season and lasted less than two years, losing his job just days before he was due to lead the team out in the League Cup final. Reflecting on his time at the club, he suggests the empty stadiums during the Covid-19 lockdowns made it impossible for him to develop the same human connection he had at Stamford Bridge.

Spurs were languishing in the bottom half of the Premier League table when Mourinho took over from Pochettino in November 2019. They had climbed to 8th by the time the season was paused amid the first lockdown, and the Champions League-winning boss told Corriere dello Sport about how that impacted his relationship with the fanbase.

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"I have a very special relationship with all my former clubs, except for one," the 63-year-old said. "My time at Tottenham coincided with the Covid period. There was no human connection.

"The stadium was almost always empty. We played two or three matches with fans, then without fans, with no interaction. I didn’t have that connection with Tottenham."

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After leaving Tottenham, Mourinho spent more than two years at Roma and one season at each of Fenerbahce and Benfica. He left the latter in the summer of 2026 to rejoin Real Madrid, the club he previously managed between 2010 and 2013.

"With Inter, Roma, Chelsea, Manchester [United], Benfica, I always felt at home. Even when I left without wanting to leave," he said. "It hurt me leaving Roma. But there isn’t, and never will be, a word from me against Roma or its people.

"I said sorry after a negative comment about [sporting director] Tiago Pinto, and that’s it. When I leave a club, I leave with a clean slate even if it doesn’t seem that way, and I leave with the feeling that it will forever be my home."