Novak Djokovic suffered two defeats in a day as his hopes of a Golden Slam came crashing down in singles before he lost in mixed doubles.
The first defeat is likely to sting more. Djokovic, who has already won the Australian and French Opens and Wimbledon this year, looked set for the gold medal match but let a lead slip against Alexander Zverev.
Djokovic, the world No. 1 from Serbia, was a set and a break up against the German fourth seed but collapsed in spectacular fashion to lose 10 of the last 11 games in an agonising 6-1 3-6 6-1 defeat.
In the knowledge he had let an opportunity to become the first man to win all the majors and Olympic gold in the same year, Djokovic then returned to court alongside compatriot Nina Stojanovic in mixed doubles.
They were beaten 7-6 (7-4) 7-5 by Russian Olympic Committee pair Aslan Karatsev and Elena Vesnina, despite leading by a break in the second set.
Djokovic will now play for two bronze medals over the weekend and still can win the Calendar Slam at the US Open in September, but he couldn't hide his disappointment at the result.
'Tough day, a really tough day. I feel so terrible right now,' said Djokovic. 'My game fell apart.
'I was leading a set then a break and he managed to turn the match around, he served huge, was attacking, and I was not getting any free points on my first serves and I missed a lot of first serves from 3-2 in the second.
'To play someone of his quality, of his level, it's just too tough to win a match.
'I just stopped, allowed him to dictate, my first serve percentage was low. At this level, with the pressure of playing for your country at the Olympics…
'Look, I didn't come here fresh, I came here exhausted emotionally, but very motivated and with a great desire to win a medal for my country. I hope to use at least one of the chances tomorrow.'
Karatsev and Vesnina will go on to face compatriots Andrey Rublev and Anastasia Pavlyuchenkova in the mixed doubles final.
Djokovic and Stojanovic will meed Aussie pair John Peers and Ash Barty as Djokovic goes for double bronze this weekend.
In the men's doubles, Mate Pavic and Nikola Mektic claimed gold, beating fellow Croats Marin Cilic and Ivan Dodig 6-4 3-6 10-6.
Switzerland's Belinda Bencic will go for double gold on Saturday.
She will face two Czech opponents. Marketa Vondrousova awaits her in the singles final before top seeds Barbora Krejcikova and Katerina Siniakova lie in wait for Bencic and Viktorija Golubic in women's doubles.
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