Cristian Garin vs. Juncheng Shang – Scheduled for 6:00 am ET

I backed Shang twice in Eastbourne last week. The talented lefty put together a very nice run, earning wins over Tomas Martin Etcheverry and Emil Ruusuvuori. He also battled extremely hard in a loss to eventual champion Taylor Fritz, losing two tiebreakers in a match that could have gone either way. The problem here is that Shang is facing a player that has really enjoyed playing at Wimbledon. Garin is mostly known as a clay-court player, but he made the quarterfinals of this event in 2022. And overall, his record at the All England Club is rather impressive, if you include his performance in qualifying. Garin is 9-0 in qualifying at this event, which is interesting considering he hasn’t had much success in any of the tune-up events on this surface. But Garin’s ability to hit powerful, flat strokes makes him dangerous in these conditions, and I trust him to get the job done against Shang. Garin has an edge in overall ability and experience. That should be enough to help him get the job done.

Bet: Garin ML (+100 – 1.5 units)

Alex Bolt vs. Casper Ruud – Scheduled for 6:00 am ET

I’m one of the biggest Ruud fans you’ll find, but I’m still playing Bolt to cover a 4.5-game spread. It’s just hard to ignore that Ruud is 2-5 at Wimbledon in his career, and he’s also 4-7 on grass overall. In fact, Ruud is so uncomfortable on grass that he generally takes the short grass-court season off. He prefers to use the time to rest and recover. With that in mind, Ruud is always in danger of being upset early in this tournament. He just comes in with no match play under his belt. Meanwhile, Bolt played a heavy grass-court schedule, competing in Surbiton and Nottingham Challenger-level events. Between those two tournaments and Wimbledon qualifying, Bolt is now 8-2 on grass this season. That success is more than enough for me to back him to keep this match close. And I really wouldn’t be surprised if Bolt wins outright.

Bet: Bolt +4.5 Games (-112 – 1.5 units)

Charles Broom vs. Stan Wawrinka – Scheduled for 8:00 am ET

The logic behind this one isn’t too different from the Ruud match. Wawrinka hasn’t played since the French Open, meaning he hasn’t played a single match on grass this year. However, while Ruud was on fire before taking this short break, Wawrinka was the opposite. The veteran has lost six of his last eight matches, making him ripe for an early exit in London. And Wawrinka is playing against a British player that has played 13 matches on grass this season. Broom is very comfortable playing on this surface and should take advantage of that here. The 26-year-old just needs to focus on hitting his spots on his serve. He can occasionally struggle with the ball on his racquet, which is not what you want on grass. But I don’t have a lot of faith in Wawrinka holding easily either. And I’m very worried about the veteran’s ability to maneuver himself around these quick courts. Wawrinka needs time to load up for his groundstrokes, especially on the side of his one-handed backhand. He won’t have that here.

Bet: Broom ML (+130)

Sonay Kartal vs. Sorana Cirstea – Scheduled for 10:00 am ET

Cirstea has looked lifeless recently. The world No. 29 comes into Wimbledon on a five-match losing streak, and that includes two matches on grass. Cirstea didn’t win a single set in Birmingham or Eastbourne, and she now faces a hometown player that is in good form entering this event. Kartal was able to make it through qualifying and finished it off with a 6-3, 6-1 win over world No. 99 Erika Andreeva. That was the first top-100 win of her career, and I like her to pick up a second here. Kartal has just played a lot more grass-court tennis this season, with the Brit having played nine matches on this surface thus far. A lot of people wanted Kartal to get a wild card into this tournament, but going through qualifiers allowed her to find her form and get comfortable in these conditions. Now, she’ll look to utilize her mobility and super-heavy forehand to take advantage of a player that is really lacking in form.

Bet: Kartal ML (+102 – 2 units)