Andy Schooler will be previewing each day’s action at Wimbledon 2026. Here’s his look at the matches taking place on day one at the All England Club.
Today's Wimbledon tips: Monday June 29
1pt Marin Cilic to win the first set v Daniil Medvedev at 13/8 (BoyleSports, Spreadex, Sporting Index)
1pt Adam Walton to beat Dino Prizmic at 6/5 (General)
Marin Cilic v Daniil Medvedev
I’m keen on getting with Cilic in some way in this contest.
The former Wimbledon finalist should prove a tricky opponent for Medvedev, a player who has never been truly at home on grass.
This season, he’s already lost to Daniel Altmaier and Kamil Majchrzak on this surface, while it’s also worth pointing out his recent struggles at the Grand Slams – four of the last five have seen the Russian exit in round one.
Cilic, a quarter-finalist in Den Bosch in the lead-up to this tournament, is 12/5 to make that five of six, which is worthy of consideration.
While it’s fair to say his best days are behind him – that Wimbledon final defeat to a certain Roger Federer was now nine years ago – he showed what he is still capable of here just 12 months ago when he caused a big upset by taking down Jack Draper (I remember backing him at a big price that day).
He went on to make the last 16 and I’m sure he’ll be relishing the chance to play here in SW19 again.
Cilic pushed Medvedev to five sets here in 2021 – he led by two sets to love – and while he did admittedly lose to the Russian in Den Bosch a few weeks ago, again the match went to a decider.
Perhaps +4.5 on the game handicap is worth taking but my preference is to back Cilic to win the opening set at 13/8.
Medvedev has now lost the first set in 11 of his last 18 matches, while his poor Grand Slam run is also reflected in this statistic, with eight of his last nine matches at the majors seeing him fall a set down early on.
Adam Walton v Dino Prizmic
Prizmic made a name for himself by defeating compatriot Novak Djokovic at the Rome Masters earlier this season but I get the impression he’s still being priced up on that win.
The Serb has won only two of his five following matches, with his sole grasscourt tune-up bringing defeat to Rinky Hijikata at Queen’s Club.
That is one of just three matches on this surface in his career. Only one win has been posted and that against a player ranked outside the world’s top 200.
Those contests have seen him face a total of 30 break points – the serve that worked well against Djokovic clearly not delivering the sought-after rewards.
His power certainly has the potential to topple Walton but the Australian has much greater experience on grass and arrives here with confidence renewed following three victories in Mallorca last week, including one over Nick Kyrgios.
Last season, he was very competitive against Carlos Alcaraz at Queen’s Club, losing 6-4 7-6 in a match featuring just the one break of serve.
To me, Walton just looks like an underdog who could well deliver and I’m happy to back him at odds-against.
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Preview posted 1855 BST on 28/06/2026
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