Team Europe came from behind against Team World on the final day of the Laver Cup to continue their dominance in the competition.
There was concern heading into Sunday when Nadal pulled out of the event through injury, preventing him from partnering up with Federer for the second time in history.
The first time the two sporting legends joined forces on the same side of the net was in the 2017 Laver Cup and it caused a frenzy among tennis fans.
But with Nadal pulling out, Tsitsipas stepped up to take his place to partner Federer on Sunday.
They were unable to beat Team World’s duo of John Isner and Jack Sock with Tsitsipas also losing alongside Nadal a day earlier.
Despite losing both doubles matches, Tsitsipas can walk away being able to say he played competitive doubles with both Nadal and Federer.
The Greek star has often played doubles this year, most notably partnering Nick Kyrgios at the Citi Open and Cincinnati Masters.
But when asked who he would prefer to double up with again in the future between Nadal and Federer, the 21-year-old needed a bit of a push to give an answer.
“You’re putting me in a difficult situation right now because I actually enjoy playing with them both so much,” he said.
“They’re both returning unbelievably well.
“Roger’s returning great, Rafa as well…
“I have to choose? Ok let me think…
“I’ll pick erm… I’ve been idolising Federer since a young age and having him as my doubles partner is a dream come true.
“Same stands for Nadal because of his energy on the court and I really feel similarity with Rafa.
“When I’m on the court I feel like with we have this Mediterranean connection I would say and very emotional both of us.
“But just because I grew up idolising Federer and, not trying to be like him, but trying to take a few things that could help my career as well, I would pick Federer.”
