The WTA Wimbledon first-round qualifying competition begins on Tuesday. It’s the most prestigious tournament in tennis, known as The Championships in Great Britain. One interesting thing about Wimbledon qualifying, as opposed to the main draw itself, is that qualifying is not held on the grounds of the All-England Club, where the main draw occurs. Qualifying is held at Roehampton. The reason for this is simple enough: Wimbledon wants its courts clean and not chewed up for the start of the main draw, which will be this year on Monday, June 29. Roehampton hosts three days of qualifying through Thursday. Many dozens of players will try to be part of the 128-member field for the summer’s big lawn tennis party. There is abundant Wimbledon coverage at Last Word on Sports. Here are LWOS’ best bets for three matches. Post your best bets and thoughts in the comments.
WTA Wimbledon
Brace – Day: 7:30 EST
H2H: 1-1
Cadence Brace faces Kayla Day in a match between the two newest players at Wimbledon. The biggest difference between these two players is not the gap in the WTA world ranking, which is close to 80 spots (Day being higher). It’s the number of matches they have played in 2026. Day has played 27 more matches than Brace, 42 to 15. Day is 31-11 in her 42 matches played this year, and Brace is 7-8 in her 15 matches in 2026.
Best Bet to Make
The books see this one in favor of Kayla all Day long, pun intended. As of now, Day is a 1.25-4 favorite on at least three different books. The average is about 3.81 to 1.24. There simply isn’t a lot of information on either woman, so this one is for degenerates only. Don’t worry, I am one of you. I speak for all of us when I say, “I’ll bet on that anyhow.” This will be the first grass meeting between these two and only their fourth combined match on grass, with the other three all having been played by Day. That’s why she’s got the nod on the books.
That being said, betting on Day winning 2:0 is a value bet for sure.
Value bet/ the best odds: Day winning 2:0 @1.75 @1xBet
Ma – Andreeva: Time 7:30 EST
H2H: 1-0
Yexin Ma faces Erika Andreeva. Neither player has played a grass match this season, instead choosing to play lower-level tournaments on other surfaces. Both players are 1-3 in their last four matches. Ma is ranked close to 50 spots higher than Andreeva (189 to 238), but Andreeva is the solid moneyline favorite at a 1.50 price. This might be due to the fact that Andreeva won 13 matches in the clay season, whereas Ma won zero matches on the surface. Of course, this is grass and not clay, but Andreeva has nevertheless done more winning in recent weeks and months. It will be fascinating to see how these players perform on grass with no prior 2026 experience on the surface.
Best Bet to Make
The fact that Andreeva did a lot more than Ma on clay might mean something, if only because Andreeva has been winning more matches this year and has shown better recent form, but with both players being unfamiliar with grass in 2026, that puts a different spin on things. Do we really know that Erika Andreeva will play a strong match on grass or that Ma will play a terrible one? It feels very uncertain, and it seems Andreeva is getting a little too much respect from the betting markets. You could go with Ma plus 1.5 sets for a decent price, but the best play in these weird and uncertain situations is always over 2.5 sets. If you’re not really sold on either player and feel the match should be priced a lot closer to a toss-up than it actually is, the over 2.5 set bet is a regularly good play to make. The price for this particular over 2.5 set bet is especially good. You will often get something from 2.45 to 2.50, but this one is special.
That being said, betting on over 2.5 sets is a value bet for sure.
Value bet/ the best odds: over 2.5 sets @2.60 @Unibet
Giovannini – Stefanini: Time 7:30 EST
H2H: 0-0
Luisina Giovannini faces Lucrezia Stefanini. The first thing that jumps out about this match and the profiles of the two players is that Luisina Giovannini plays almost exclusively on clay. She has played 40 professional matches this year, and of the 40, 38 were on clay. She played two on hardcourts. That’s a ton of clay tennis, and with hardly any hardcourt matches, that really shows how much Giovannini wants to play on clay. Hardcourts are the most commonly used surface on tour, even more than clay. It’s very common for players to not play on grass because it is such a rarely-used surface with a very short season, but it’s a lot less common for players to ignore hardcourts and stick to clay. This is a grass match, but we bring up the point about Giovannini not even playing much hardcourt tennis because it reinforces the idea that she is a one-surface player. It’s not just being a specialist but being someone who really does focus on only one surface. Will that matter here?
Best Bet to Make
The WTA world rankings are nearly identical for these players, 163 and 166. However, the lopsided nature of Giovannini’s clay match participation versus all other surfaces suggests that she will be very uncomfortable on grass. Stefanini has played matches on all surfaces this season, in what is a much more balanced profile. She won one grass match on June 9 and is 1-1 on grass. It’s not a dazzling or very impressive profile, but it shows a small willingness to play on grass. Giovannini is likely to be the less comfortable player, and that’s why it’s really hard to make a pro-Giovannini bet of any kind. Stefanini to win in straight sets is the play to make here.
That being said, betting on Stefanini winning 2:0 is a value bet for sure.
Value bet/ the best odds: Stefanini winning 2:0 @2.04 @1xBet
Main Photo Credit: Susan Mullane-USA TODAY Sports
