Wimbledon 2026 PREVIEW & PREDICTIONS | Monday Match Analysis

**Gill Gross** (0:01)
Welcome, everyone, to Monday Match Analysis. I'm Gill Gross, and it is time for a preview of Wimbledon 2026 We'll go quarter by quarter with dark horses, upset alerts, popcorn matchups, quarterfinal predictions, and final weekend predictions ahead of this always special third major of the year at the irreplaceable All England Club, coming off of a Roland Garros, which was the most chaotic slam on the men's side in recent memory. We had a quarterfinal between two unseated players. We had four first time major quarter finalists, a first time slam finalist, and a first time major champion.
And the crazy thing about that is if you look at the data, and I've seen this fly around the betting community because they obviously are going to track which tournaments are good for favorites, which tournaments are good for underdogs. Roland Garros and Australian Open, and I've observed this even without the data, I would have suspected this. Those are the two slams where things tend to go as expected, seeds tend to hold, the top players tend to take care of their business. And historically, where things get a whole lot more unpredictable is Wimbledon and the US Open. But right now, we're at a phase on the tour where I think anybody can see that between five and twenty, maybe even up to twenty-five, it is a lot muddier than it usually is. I think typically if you said you've got to put your life on a player making the quarters, there would be four or five guys where you feel okay about that. Okay. They have to make the quarters for my life. All right. Normally, I think four or five players who you might feel decent. Right now, there's probably only one. Other than that, you're sweating. So with that, let's get into it. Jannik Sinner's quarter, he's the top seed. He comes off of his disappointing and dramatic role on Garo's exit. Still slamless on the year, which is insane, given how good a year he's had elsewhere. He is with Medvedev, Rude, Daugherty, Paul, Hodar, Nakashima and Busse. My dark horse in this quarter is Ethan Quinn and Hamad Majedovic. And I'll explain why I annotated the rounds in a moment. My upset alert is Caspar Rude. My early popcorn is Medvedev vs. Chilich in round one. So on the dark horse situation, I feel as if Majedovic is a sure thing to get to the third round. I feel more confident about that. But I feel more confident in Ethan Quinn if you're looking at which unseeded player is most likely to make the fourth round. So let me start with Quinn, who's in the final in Majorca.
But on grass, I'm a lot less worried about fatigue. I'm not really worried about a massive emotional letdown either with Ethan just knowing a little bit about his mental makeup.
I look at his path facing Luciano Daugherty in the first round. I think it'll be Shintaro Mochizuki, who's a fascinating player in the second round. Flawed player, very interesting player, came through qualifying. I recommend you watch him play. It's really entertaining. That's Mochizuki. And then Hodor in the third round. Hodor, I really love his returning on grass. And I think the way he returns is going to give him a chance to do some serious damage on the surface in the future. But he's missed a lot of training trying to get that abdominal injury right. I hate ab injuries. I think they're pretty destructive, especially on the serve. And he's got very little grass experience to begin with.
And his serve, not being very precise, that'll hurt him at this stage in his career as well. So I just look at three matchups for Quinn, and I don't think he's a huge underdog, or really a solid underdog in any of them. I think he's right there in all of those matchups. Although I don't discount Daugherty as just a clay quarter, he's got a huge serve, he's a flat hitter, he's got a massive forehand. Is he a little bit rushable? Yes. Does he need some time on the ball normally for his return? Yes. But it wouldn't shock me if it's Daugherty in the fourth round, if he gets through Quinn. But anyway, Hamad Medvedevich, also a dark horse in this quarter.
I don't know if he's going to be rushable on the grass. He's had some success on the quicker surfaces, but he's had a little bit more of his success on the clay, believe it or not. And his level during this clay swing was absolutely scary at times.
He has incredible offensive tools and an enormous first serve, a massive forehand and really great feel. Awesome drop shots, good drop volleys when he does get up to the net. Not the most athletic guy doesn't defend much, but on grass that is not as important. You want to get in attack, good shots are rewarded. Again, I don't know if that forehand is going to be, and the backhand honestly, I don't know if he's going to feel a little bit rushed in these conditions, but if not, I think he's a good bet to make the third round. He gets Sebastian Offner in the first round, the winner of Huracach and Ruud in the second round. We'll talk about that one in a moment, and then it would be Tommy Paul in round three. Martin Landolusse is also a candidate for Dark Horse in this quarter. Lots of grass experience for a 20-year-old, and he's played his best at big events. He's got some splashy results this year. No major weaknesses. I don't think the explosiveness is there for Landolusse, and I do think the fact that he's had just a couple of big runs with a spotlight on him, as great as that is, I'm a little bit lower on him probably compared to the general sentiment. Caspar Roode is my upset alert.