However, the Portuguese hopes to see his club boss Massimo Moratti shed tears of joy with a first European Cup success in 45 years for the Italian side on Saturday night.
Mourinho was tearful after eliminating the West Londoners following a 1-0 win in the last 16 at Stamford Bridge back in March, realising he had ruined the dream of many of his close friends.
"At Stamford Bridge I cried because during the 90 minutes I wasn't thinking that I was playing against friends, but after the game I realised I that my friends were out of the competition," he reflected ahead of Saturday's Champions League final against Bayern Munich.
"But that was crucial for Inter, without that victory we wouldn't be here today - it was a difficult emotional situation," he added.
Victory over Bayern at the Santiago Bernabeu is likely to produce tears of a different kind, however, and Mourinho would be proud to see Inter boss turn on the waterworks after a 45-year European Cup drought.
"Defeat or victory, it will be unforgettable, but Moratti is a very special person for me," he said.
"I would love to see him cry (with joy), I would love to see him with the cup in his hands, I would love to see him in a picture next to his father; I would love to give my little contribution to help make that happen," he explained.
Inter's current boss is son of former club owner Angelo Moratti, who led the Italians to back-to-back European Cup titles in the 1960s.
Success was hard to come by initially under Moratti jnr, but recent times have been more prosperous, especially this season.
Mourinho's "little contribution" has already seen the Milanese outfit capture the Serie A title and the Coppa Italia this season, but the Portuguese coach knows Saturday's final is the big one.
"45 years is 45 years - it's a long time," he said.
"Many of Inter's fans cannot remember that far back and many were not even born when the club last won the European Cup.
"The Champions League final is always important and you want to win it even if you won it last year, but I imagine that for these fans it will be even more special after such a long wait," he added.
And even though the Portuguese has had a bumpy ride in his time in Italy so far, he claims nothing would give him greater pleasure than winning a Champions League title for Inter.
"It's a special club with a special president and special fans, and I want to be part of that," he said.
But the 'Special One' was his usual colourful self in the press room and he reserved a wicked taunt for Bayern, who have already celebrated two domestic titles of their own.
"Bayern had the party and the bus (celebration)," he said.
"We haven't had a party or a bus."