Carlos Alcaraz suffers shock defeat to Grigor Dimitrov in latest Shanghai Masters upset – ‘I knew what I had to do’

World No. 2 Carlos Alcaraz is out of the Shanghai Masters after falling to a 7-5 2-6 4-6 defeat to Grigor Dimitrov in the last 16.

Dimitrov’s biggest win of the season earned him a spot in the quarter-finals despite coming into the match trailing the Spaniard by three matches in the pairs’ head-to-head record.

Alcaraz was aiming for his 13th quarter-final in the 14 events he has played so far in 2023 and his seventh title of the season, but Dimitrov claimed he “knew what he had to do” to overcome the two-time Grand Slam champion.

“I stayed in the match, that was the first thing, especially after the first set,” he said, reflecting on the opening set that he lost. “I was serving very well throughout the first set and he made a few errors.

“I pushed him to make a lot of errors at certain moments. At 4-5 he played an amazing game and another at 6-5. I was creating a lot of opportunities.

“After the second break in the second set, I think I understood his service games and was able to put more balls in and read his serve a bit better.

“I think in the third set it was a bit of cat-and-mouse. I think we both played a solid set. He made a few errors and I was very solid and served well when I had to.

“I knew what I had to do. I knew I had to apply constant pressure against him. Even if I was down, even if my shots were not good enough, I had to put him in uncomfortable positions.

“He doesn’t like being on the back foot. I was coming in quite a little bit and trying to put him in awkward positions.”

The 32-year-old looked in good form and led 5-3 in the first set before Alcaraz came from behind to win it via a tie-break.

But Dimitrov’s positive form would follow through into the second and third sets of a tight battle, which the Bulgarian edged with his low slices into the net, tactical backhand drop shots and reliable service game.

Dimitrov hit 29 winners to reach his first Masters 1000 quarter-final of the season, and it was the 17th in his career overall as he claimed only his fourth top-two win.

He will next face 22nd seed Nicolas Jarry in a bid to win his first title since 2017.

Despite a nightmare showing on the Asian tour – losing a China Open semi-final to Jannik Sinner before his last 16 exit to Dimitrov – Alcaraz still hopes to overtake rival Novak Djokovic and finish the year as world No. 1.

“It’s been complicated for me to finish the year as No. 1, but I will try to do my best in Basel, which will be my next tournament,” he said after defeat to Dimitrov. “It’s going to be difficult but I want to try.”