Wimbledon Picks & Predictions Today (June 29)

• Tommy Paul offers actionable spread value at -8.5 against Alexandre Muller
• Is Casper Ruud a live underdog against Hubert Hurkacz?
• See my top Wimbledon picks and predictions for Monday’s men’s singles matches

The 2026 Wimbledon men’s singles draw gets underway at the All England Club on Monday, June 29, with a packed slate of matchups. The first Round of 128 matches start at 6:00 am ET, while the final showdown of the afternoon gets underway at 12:00 pm ET.

Today’s slate features several of the sport’s biggest stars stepping onto the court as massive betting favorites. Headlining the action, top-ranked Jannik Sinner takes on heavy underdog Miomir Kecmanovic, while Novak Djokovic closes out the day on Centre Court against another massive underdog in Yibing Wu.

I have analyzed the odds to find positive-expected value (+EV) bets. The table below summarizes my three Wimbledon best bets for June 29. Under the table, find my rationale for each pick and, at the tail-end, the full odds for today’s first 20 matches.

Wimbledon Picks Today (June 29) – Men’s Singles

My picks today include one moneyline underdog, one heavy favorite to cover a big spread, and the world #1 to make quick work of an overmatched opponent.

Looking for tournament outrights? Check out SBD’s odds to win Wimbledon.

Ruud vs Hurkacz Pick: Ruud Moneyline 35¢ (+186) at Kalshi

I am backing Ruud on the moneyline as a live underdog. At +186, the market gives Ruud an implied probability of 35%, recent form makes the underdog worth a shot.

Ruud’s lack of grass reps is the obvious concern. His only listed grass match in this recent sample was a 6-3, 6-4 Hurlingham exhibition loss to Ben Shelton, and his best results over the past two months have come on clay. Still, that clay stretch was strong enough to matter: he reached the fourth round at Roland Garros with wins over Roman Safiullin, Hamad Medjedovic, and Tommy Paul, then lost a four-setter to Joao Fonseca.

Before that, he stacked wins in Geneva and Rome, including victories over Alexei Popyrin, Jenson Brooksby, Lorenzo Musetti, Karen Khachanov, and Jiri Lehecka. That gives him a recent base of match fitness, rally tolerance, and return rhythm that can translate if Hurkacz’s first-serve percentage dips.

Big-serving Hurkacz owns the more natural grass-court profile, but his recent results are far from dominant. He beat Andrey Rublev in Halle and Sebastian Baez in a Boodles exhibition, yet also lost to Marton Fucsovics in Hertogenbosch, Daniel Altmaier in Halle, and Jakub Mensik in another grass exhibition. Since the start of the spring, his results have been volatile across surfaces, with early losses to Ethan Quinn, Aleksandar Kovacevic, Luciano Darderi, Lorenzo Musetti, Frances Tiafoe, and Altmaier mixed around a few quality wins.

The head-to-head also matters: Ruud beat Hurkacz 7-5, 6-3 at the United Cup on Dec. 30, 2024. That was on hard court, not grass, but it reinforces that Ruud can handle Hurkacz’s pace when he gets enough returns in play. I expect Hurkacz to win plenty of cheap points behind the serve, but if Ruud extends return games and forces second-shot execution, the underdog has a cleaner upset path than the market suggests.

Paul vs Muller Pick: Paul -8.5 Games 51¢ (-104) at Kalshi

Tommy Paul profiles as a massive favorite poised to eliminate Alexandre Muller without breaking a sweat, and the recent grass-court sample backs up the gap. Paul went 4-1 at Queen’s Club/London this month, beating Zachary Svajda, Botic van de Zandschulp, Alejandro Davidovich Fokina, and Ugo Humbert in succession before a three-set loss to Francisco Cerundolo. Including last year’s grass swing, Paul is 5-3 in grass matches dating back to Eastbourne/Wimbledon 2025, and he also split two recent grass exhibitions, beating Arthur Fils before falling narrowly to Novak Djokovic.

Muller’s grass profile is much thinner and far less encouraging. Dating back to last grass season, he is 0-3 on the surface in official matches, losing to Alexander Bublik in Halle, Roman Safiullin in Mallorca and Djokovic at Wimbledon while taking just one set across those three matches. He also enters this spot without a listed grass tune-up this season and has been stuck in a poor run overall, dropping seven straight completed or retired matches from mid-April through Roland Garros.

My projections grant Paul a dominant 95.7% win probability, and this matchup sets up well for a lopsided scoreline. Paul’s first-strike forehand, athletic return game, and comfort moving on grass should let him pressure Muller’s service games immediately. With Muller short on recent wins and lacking grass rhythm, the statistical and surface-form disparity points to Paul winning with ease and covering the 8.5-game spread.

Sinner vs Kecmanovic Pick: Under 30.5 Games 59¢ (-144) at Kalshi

Instead of laying heavy juice on the Sinner moneyline, I am attacking the Under 30.5 games total.

The recent form gap is massive. Sinner’s lone grass tune-up in this sample was a clean 6-3, 6-3 exhibition win over Cameron Norrie on June 24, and his 2025 grass résumé is even more compelling. He won Wimbledon last year, beating Lorenzo Nardi, Aleksandar Vukic, Pedro Martinez, Ben Shelton, Novak Djokovic, and Carlos Alcaraz while dropping only one completed set across that title run. His most relevant matchup note is even louder: Sinner swept Kecmanovic at Wimbledon in 2024 by a 6-1, 6-4, 6-2 scoreline, a 25-game result that would clear this Under with room to spare.

Sinner’s broader 2026 form also supports a short match. Before Wimbledon, he stacked clay wins over Sebastian Ofner, Alexei Popyrin, Andrea Pellegrino, Andrey Rublev, Daniil Medvedev, Casper Ruud, Arthur Fils, Alexander Zverev, Felix Auger-Aliassime, Tomas Machac, Ugo Humbert, and Carlos Alcaraz. Even his heat-induced French Open stumble against Juan Manuel Cerundolo came in five sets after he had opened the tournament with a routine straight-sets win over Clement Tabur.

Kecmanovic brings more volatility than upside. His recent grass stretch includes a Halle loss to Fabian Marozsan, two wins in Mallorca over Andrea Ghibaudo and Lorenzo Sonego, then another straight-sets loss to Marozsan on June 25. He did reach the third round at Wimbledon last year, but Djokovic erased him 6-3, 6-0, 6-4, and Sinner produced an even more dominant straight-sets win over him at the same event in 2024.

Kecmanovic can extend rallies and has enough baseline craft to avoid a total collapse, but this matchup asks him to protect serve repeatedly against the best return-pressure player in the draw. If Sinner starts fast and lands one early break per set, a scoreline in the 6-3, 6-4, 6-3 range is well within reach. That keeps the Under 30.5 firmly in play.

The table below lists the full odds (moneyline, game spread, total games) for the first 20 matches on the men’s singles docket on Monday, in case you want to scour the board for yourself.

Wimbledon Odds – Men’s Singles (June 29)

All lines presented above are provided by bet365.