Federer saved five match points in the second set and received a point penalty in the third in the 6-3, 6-7 (7), 6-3 loss to fifth-seeded Alexander Zverev.
The second-seeded Federer, who is bidding to win a third Shanghai Masters title, dominated in the first set, but was tested in the second.
Swiss tennis star Roger Federer will take on Germany's Alexander Zverev in an exhibition duel as part of a Latin America tour.
Both Federer and Nadal have enjoyed unprecedented success in men's tennis and have 20 and 19 Grand Slam titles respectively.
Tennis legend Roger Federer on Saturday asked his fans to suggest a new profile picture for his Twitter account.
Roger Federer expressed his desire to watch a 'Bollywood classic', and the fans have since been providing him with movie suggestions!
Roger Federer and Alexander Zverev won on the final day as Team Europe retained the Laver Cup title.
Rafael Nadal came to the decision following consultation with the Laver Cup competition doctor.
The Laver Cup is turning out to be an absolute delight for tennis fans, as the second day of the tournament saw Rafael Nadal giving pep-talk to Roger Federer to help him defeat Team World's Nick Kyrgios.
Roger Federer and Rafael Nadal were seen coaching Fabio Fognini during his Laver Cup game against Team World's Jack Sock.
Roger Federer and Alexander Zverev combined to beat Jack Sock and Denis Shapovalov 6-3, 7-5 to give Team Europe a 3-1 lead over Team World in the Laver Cup.
It will be only Roger Federer's second appearance in Colombia, coming seven years after he beat Frenchman Wilfried Tsonga in an exhibition duel in Bogota.
Eight teams among the 24 participating in the group stage, will advance to the knockout rounds, which will continue in Sydney until January 12.
Grigor Dimitrov defeated Roger Federer 3-6 6-4 3-6 6-4 6-2 to set up a semi-final clash with Daniil Medvedev.
Daniil Medvedev went past Stan Wawrinka 7-6, 6-3, 3-6, 6-1 on Tuesday despite 12 double-faults and a body that's just short of breaking down.
Federer said he loves coming to India not only to visit but also to play.
Roger Federer made light work of David Goffin with a 6-2, 6-2, 6-0 win while Serena Williams defeated Petra Martic 6-3, 6-4 in the pre-quarters of US Open.
Roger Federer defeated Dan Evans 6-2, 6-2, 6-1 in the third round of US Open but denied that he chose timing of the match.
Nagal said that clay was his preferred surface, something that Federer himself had pointed out after the match.
Novak Djokovic fought pain to seal his 6-4, 7-6, 6-1 win over Juan Ignacio Londero while Roger Federer won 3-6, 6-2, 6-3, 6-4 against Damir Dzumhur in the second round of US Open.
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