World number five Tsitsipas lost 7-6 (9/7), 7-5 to Chilean Nicolas Jarry, ranked 28 in the world.
It marks the third consecutive time the Greek has been knocked out in the second round of the Wimbledon warm-up tournament.
Medvedev defeated Serbian Laslo Djere 6-3, 6-7 (5/7), 6-3, with the world number three overcoming losing a tight second set to win with ease.
“Grass is so tough for me,” said Medvedev, when asked about how he handled the surface during his win. “You can actually play a perfect match and lose on two tie-breaks, so it’s a little bit strange for me. When I see top players like Roger (Federer), from one side they can seem like aliens but you try to see the best in them, and how they are able on this surface, where it’s sometimes tricky to beat anyone, to have so many titles. Wimbledon, Halle, whatever.
“It’s just amazing and that’s what I try to watch. Happy to win and looking forward to the next matches.”
The former world number one and 2021 US Open champion was runner-up on the Halle grass in 2022, losing to Hubert Hurkacz in straight sets in the final.
Medvedev has struggled on grass in his career so far and has never reached the quarter-finals at Wimbledon.
He will next face Spanish eighth seed Roberto Bautista Agut.
He missed last year’s tournament at the All England Club due to Wimbledon’s ban on Russian and Belarusian players competing.
Medvedev has won five ATP titles already this year, but was beaten by Sebastian Korda in the Australian Open third round and was dumped out in the French Open first round for the fifth time in seven appearances.
Home favourite Norrie rallies past Thompson at Queen’s
Cameron Norrie dug deep in front of his home fans yesterday to deny Jordan Thompson a second-round upset at the Cinch Championships.
The fifth-seeded Briton prevailed 4-6, 6-3, 6-2 against Thompson at the Queen’s Club to reach the quarter-finals for the second time at the grass-court ATP 500. Norrie won 10 of the final 13 games of the match to complete an impressive turnaround after ‘s-Hertogenbosch finalist Thompson had taken charge in west London.
“I think it was the perfect match,” said Norrie. “Jordan obviously really likes the grass and he played a really solid first set. He played a couple of good points to break me, and I played a couple of loose points, and that was the difference in the first set. I actually thought I played great, so I didn’t really have to change too much.
“He dropped his level slightly (in the second set). I came up with a few points and it was just like classic grass-court tennis. I was able to come out with a lot more energy in that third set and I think that was the difference. There wasn’t much in it, and it was a really good match to get through.” With his one-hour, 58-minute win Norrie improved to 31-11 for the 2023 season. The 27-year-old lifted his maiden ATP 500 crown on clay in Rio de Janeiro in February and will take on fourth seed Frances Tiafoe or Sebastian Korda next as he chases his first tour-level grass-court title at Queen’s, where he reached the championship match in 2021.
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