MELBOURNE, Australia — Rafael Nadal’s bid for a record 21st Grand Slam men’s singles title ended Wednesday night when he lost to Stefanos Tsitsipas of Greece in the quarterfinals at the Australian Open.

Tsitsipas dropped the first two sets but came back to defeat Nadal, the second-ranked player in the world, 3-6, 2-6, 7-6 (4), 6-4, 7-5, in a grueling, four-hour duel for the biggest Grand Slam win of his career.

Nadal, of Spain, played a near flawless first three sets, not allowing a break of his serve or even a break point, and he appeared in full control of the match. But in the third-set tiebreaker, he missed two overheads and sent a backhand wide to give Tsitsipas the tiebreaker and a lifeline.

Then what had been a rout turned into a street fight. Playing on fresh legs after winning his fourth-round match in a walkover, Tsitsipas became increasingly stingy on his serve, refusing to give Nadal a chance to seize an advantage and forcing him into sloppy errors as he grew more fatigued.

Tsitsipas, who at 22 years old is 12 years younger than Nadal, seemed to gain energy and a bounce in his step as the warm evening wore on, getting to balls that had been out of his reach earlier and forcing Nadal to hit extra shots and battle to hold his serve in nearly every game.

In the fifth set, Nadal and Tsitsipas traded service games, with Tsitsipas’s serve becoming increasingly untouchable — he served four consecutive aces to knot the set at 3-3 — and Nadal fighting for nearly every point to stay level. Serving at 5-5

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