Monday Wimbledon Best Bets, Predictions, Analysis: How We’re Betting Day 1 of the Championships (June 27)

Monday Wimbledon Best Bets, Predictions, Analysis: How We’re Betting Day 1 of the Championships (June 27) article feature image

Adam Davy/Getty. Pictured: Wimbledon.

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The third Grand Slam event of the year is upon us as the Wimbledon main draw gets underway Monday.

This iteration of the Championships will be unique, as Russians and Belarusians weren't allowed to play in the draw due to Wimbledon's ruling.

That means players such as Daniil Medvedev, Andrey Rublev, Aryna Sabalenka and Daria Kasatkina aren't able to compete this year.

In response, the ATP and WTA Tour governing bodies elected to remove ranking points from the tournament. While there is a boatload of prize money and prestige that comes with Wimbledon, this will be a very odd situation.

With the first round set to get going, here is how our tennis analysts are playing the matches.

Matches are listed in chronological order. Match times are subject to change and many will be played after the projected start time. Read here for advice on watching Wimbledon.


Hubert Hurkacz vs. Alejandro Davidovich Fokina

6 a.m. ET

Hubert Hurkacz is a popular dark-horse pick to contend at the Championships.

Kenny Ducey breaks down his first round match, and offers a rationale for fading the young Pole.

Quentin Halys vs. Benoit Paire

6 a.m. ET

The day gets started with one of the most entertaining players on tour, Benoit Paire.

Avery Zimmerman breaks down the all-French match that Paire has against Quentin Halys.

Aljaz Bedene vs. Maximilian Marterer

6 a.m. ET

In a near pick 'em match, Jon Reid sees value in the veteran Aljaz Bedene.

See why he's backing the Slovenian to secure a result against Maximilian Marterer.

John Isner vs. Enzo Couacaud

7:15 a.m. ET

John Isner is a former Wimbledon semifinalist, but he's not as dominant at the event as many may think.

Read on to see why Luke Holmberg isn't foreseeing a great performance from the American.

Elise Mertens vs. Camila Osorio

8 a.m. ET

Camila Osorio had a successful Wimbledon campaign last year, but David Gertler isn't expecting something similar.

Read on for his best bet on her match with Elise Mertens.

Dalma Galfi vs. Maddison Inglis

8:30 a.m. ET

In a matchup of two youngsters on tour, Reid is looking for the underdog to compete better than she is getting credit for.

See why he's backing Maddison Inglis in this encounter.

Novak Djokovic vs. Soon-woo Kwon

8:30 a.m. ET

Three-time reigning Wimbledon champion Novak Djokovic gets his campaign underway against Soon-woo Kwon.

Isaac Gartzman is anticipating an easy affair for Djokovic. Read on to see why.

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Jannik Sinner vs. Stan Wawrinka

9:15 a.m. ET

One of the blockbuster first round matchups will be played between Jannik Sinner and Stan Wawrinka.

Holmberg breaks down where the value lies between the duo.

Christian Harrison vs. Jay Clarke

9:15 a.m. ET

An intriguing affair awaits American qualifier Christian Harrison as he faces wild card Jay Clarke.

The Brit will have the crowd's support, but Reid is looking at the American to produce a result.

Carlos Alcaraz vs. Jan-Lennard Struff

9:30 a.m. ET

Carlos Alcaraz opens his Wimbledon campaign up with a match against the big-serving Jan-Lennard Struff.

Ducey breaks down the intriguing match and offers some caution to those backing Alcaraz.

Sebastian Baez vs. Taro Daniel

10:30 a.m. ET

Neither Sebastian Baez nor Taro Daniel have had sustained periods of success on this surface.

See why Zimmerman is backing the experienced Daniel to fare better than his opponent in this match.

Alison Van Uytvanck vs. Emma Raducanu

10:30 a.m. ET

Emma Raducanu is one of the stories of the tournament after breaking out at Wimbledon prior to winning the US Open last year.

Gertler isn't seeing another big run out of the Brit, however, and he explains why.

Daria Saville vs. Viktoriya Tomova

11:15 a.m. ET

Rounding out the day is a match between Daria Saville and Viktoriya Tomova.

Reid likes the value that he can get on the spread. See why he's targeting that market ahead of this match.

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