ATP Wimbledon Round of 16 action continues on Monday. This is the part of the draw without Jannik Sinner or Novak Djokovic in it, so every player in this part of the draw will think he has a chance to get to the Wimbledon final. The two players who stood out as the main favorites to get to the final are Taylor Fritz and Alexander Zverev. If they win their Round of 16 matches on Monday, they will meet in the quarterfinals. They have met at Wimbledon before, so a reunion in the quarterfinals would become one of the more important and anticipated matches of the tournament. Will there be upsets, or will the higher seeds advance? Will other contenders emerge from the two other Round of 16 matches on the card? LWOS has our best bet for four matches. Post your best bets and thoughts in the comments.
ATP Wimbledon
Dimitrov – Fery: 10:00 EST
H2H: 0-0
The ATP Wimbledon Round of 16 continues with Grigor Dimitrov trying to get back to the ATP Wimbledon quarterfinals. Dimitrov has reached the semifinals of this tournament in the past, but he can’t get that far until he makes the quarters. Dimitrov has beaten quality opposition to get this far. He beat Roland-Garros semifinalist Jakub Mensik in the second round. Then he beat former Wimbledon runner-up Matteo Berrettini in the third round. He is playing good tennis and really enjoying himself at this tournament, where he got injured a year ago when leading Jannik Sinner. Now Dimitrov will try to keep the momentum going against British hope Arthur Fery, who beat Otto Virtanen (the man who beat Ben Shelton at this tournament) in the second round and then came from behind to beat Zizou Bergs in the third round. Both players are riding high and will try to stay in form as they meet in the biggest match of their 2026 seasons.
Best Bet to Make
Dimitrov did need five sets to beat Matteo Berrettini, so for that reason, some bettors might be a little afraid to pick Dimitrov to cover a set spread, but Dimitrov minus 1.5 sets seems like a very reasonable scenario here. Dimitrov is the clear favorite to win the match, something you should put into a parlay (because it doesn’t have enough value on its own), so if he is going to win, the chances of him winning in fewer than five sets are decent. You don’t have to bet on Dimitrov to win in straight sets. Dimitrov winning in four sets seems fairly probable, and the price is really good. This is the play to make.
That being said, betting on Dimitrov -1.5 sets is a value bet for sure.
Value bet/ the best odds: Dimitrov -1.5 sets @1.89 @1xBet
Fritz – Bublik: 11:30 EST
H2H: 4-4
Taylor Fritz and Alexander Bublik have met eight times, which is a lot more than most of the matchups we write about here at Last Word On Sports. Usually there are just a handful of matches between players. Eight is definitely above average for head-to-heads. This ninth meeting in the ATP Wimbledon Round of 16 will clearly be the biggest of the nine between Fritz and Bublik. The fact that the two players know each other well and have seen so much of the other’s game means this is a familiar matchup. There probably won’t be surprises. There will be an expectation of what the other player is capable of. This is something for tennis bettors to think about.
Best Bet to Make
Because these players are familiar with each other, the edge should go to the more in-form player. That’s Taylor Fritz. He won in four sets against Lorenzo Sonego on Saturday in the ATP Wimbledon third round, on a day when Sonego was playing well. Fritz served well and did the things he knows how to do. If he can keep doing that, he should be fine. Bublik needed five sets to beat Frances Tiafoe in a very up-and-down match. Bublik played well in the key parts of the match but was inconsistent overall. He was fortunate to get through that match. He never nearly lost the third set but managed to recover and win it, which helped him win in five sets. He will need Taylor Fritz to struggle to advance, and we just don’t see Fritz playing mediocre tennis in this spot. Put Fritz moneyline into a parlay, and then for the main bet, go with Fritz to win in no more than four sets, which offers a very good price.
That being said, betting on Fritz -1.5 sets is a value bet for sure.
Value bet/ the best odds: Fritz -1.5 sets @1.92 @1xBet
Lehecka – Zverev: Time 12:00 EST
H2H: 1-2
Jiri Lehecka and Alexander Zverev have not faced tough draws so far at this ATP Wimbledon tournament. Lehecka faced Alexei Popyrin, Alex Molcan, and Jaume Munar. None are in the top 40. Munar is the only one in the top 100. Zverev has faced and beaten Alexander Blockx, Valentin Royer, and Marcos Giron. Blockx is the only player of those three who is in the top 40, and he’s at 36. Neither Royer nor Giron is in the top 70. These have been good paths for both players. Now they get to test each other with a spot in the quarterfinals on the line. Lehecka has never made the Wimbledon quarterfinals, so this will be one of the biggest matches he has ever played. Zverev is trying to follow his French Open championship with another trophy at the All-England Club.
Best Bet to Make
These two players had easy first weeks at this ATP Wimbledon showcase. Now they meet. Lehecka is talented, and Zverev might be a little less motivated to win because he just won Roland-Garros. However, Lehecka has not consistently shown he can win these kinds of matches against really good opponents. If you were to bet on a winner, you would have to lean Zverev here. What you could do is go with Zverev moneyline in one parlay and then Lehecka plus 2.5 sets in another parlay, since it’s unlikely Lehecka won’t be able to win at least one set. For the main bet, Zverev -1.5 sets has a very generous price. Zverev is the No. 2 seed at this tournament. He can lose one set and still win your bet. That’s hard to pass up.
That being said, betting on Zverev -1.5 sets is a value bet for sure.
Value bet/ the best odds: Zverev -1.5 sets @1.62 @1xBet
De Minaur – Cobolli: Time 8:00 EST
H2H: 2-0
Alex De Minaur has been to the Round of 16 at the ATP Wimbledon event before. What he hasn’t done is make the Wimbledon semifinals. He needs two wins to do that. The first of two matches he will have to win comes against Roland-Garros finalist Flavio Cobolli, who beat Karen Khachanov in five sets to advance here. Cobolli has played a ton of tennis. He played a lot at the French Open on his way to the final, where he played a long five-set match against Alexander Zverev. Now at Wimbledon, Cobolli has played a total of 13 sets in three matches. He hasn’t won a match in straight sets. Cobolli must play an opponent, Alex De Minaur, whose fitness and speed are both above average. Cobolli will very likely need to get off to a good start in this match. If he falls behind, it will be a challenge for him to find the energy needed to come back and win.
Best Bet to Make
De Minaur minus 1.5 sets makes a lot of sense here, but the price isn’t high enough to be our main value bet. You can put that into a parlay. The slightly better bet, and therefore our main recommended bet, is De Minaur minus 4.5 games. If he wins the match in four sets, the chances are good that it will add up to a five-game margin. It’s not a guarantee, but it’s likely. Cobolli has played so much tennis that he is bound to get tired, and Alex De Minaur is not the player you want to be tired against. The bet here should favor De Minaur in some way, though you could put in a parlay piece for Cobolli plus 2.5 sets or something like that as a partial way to provide yourself some insurance.
That being said, betting on De Minaur -4.5 games is a value bet for sure.
Value bet/ the best odds: De Minaur -4.5 games @1.62 @Betway
Main Photo Credit: Geoff Burke-USA TODAY Sports
