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The former world champion Indian and Giri played out four draws before the Dutch player pulled off a win in the Armageddon game (a tie-break) late on Friday.
Anand, however, picked up his first point of the event. He remains at the bottom of the table. He had earlier lost to Peter Svidler, Magnus Carlsen and Vladimir Kramnik.
The Chennai-based Anand, who is making his maiden appearance at the Magnus Carlsen Chess Tour, settled for a 82-move draw in the opening game of the best-of-four contest.
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Giri grabbed the decider with black pieces to secure victory and two points.
Anand meets Hungary”s Peter Leko in the fifth round later on Saturday.
Russia”s Peter Svidler, who was in joint lead with Magnus Carlsen, lost to Ding Liren of China 1.5-2.5 to hand the sole lead to the Norwegian world No.1. Carlsen has 12 match points and is followed by Ian Nepomniachtchi (11).
It was Liren”s first win in the tournament.
Carlsen had no troubles, thrashing veteran Israeli Boris Gelfand 3-0.
All the round-robin games are best-of-four game contests.
Legends of Chess is a unique event where Carlsen, Liren, Nepomniachtchi and Giri, semifinalists at the Chessable Masters (part of the Magnus Carlsen Tour), received an automatic invite and are up against six legends aged 40-52, who have been at the top of world chess at various points in their career.
The tournament is part of the Magnus Carlsen Chess Tour. The winner of this event will qualify for the USD 300,000 Grand Final scheduled from August 9 to 20.
Results: Round 4: Anish Giri beat Viswanathan Anand 3-2; Magnus Carlsen beat Boris Gelfand 3-0; Vladmir Kramnik beat Peter Leko 2.5-1.5; Ding Liren beat Peter Svidler 2.5-1.5; Ian Nepominiachtchi beat Vasyl Ivanchuk 2.5-1.5.