{"id":107732,"date":"2026-06-29T19:06:50","date_gmt":"2026-06-29T23:06:50","guid":{"rendered":"https:\/\/lastwordonsports.com\/tennis\/?p=107732"},"modified":"2026-06-29T19:06:50","modified_gmt":"2026-06-29T23:06:50","slug":"wta-wimbledon-first-round-best-bets-including-jasmine-paolini-vs-robin-montgomery","status":"publish","type":"post","link":"https:\/\/lastwordonsports.com\/tennis\/2026\/06\/29\/wta-wimbledon-first-round-best-bets-including-jasmine-paolini-vs-robin-montgomery\/","title":{"rendered":"WTA Wimbledon First Round Best Bets Including Jasmine Paolini vs Robin Montgomery"},"content":{"rendered":"

WTA Wimbledon first-round play continues on Tuesday. Whereas the other three major tennis tournaments play their first round over three days, Wimbledon does it in only two. Wimbledon doesn\u2019t play main-draw tennis on a first Sunday. The tournament actually modernized in recent years by having play on the so-called \u201cMiddle Sunday.\u201d The two-day first round means Tuesday\u2019s schedule is jam-packed with matches. We\u2019re going to bring them to you and give you a lot to think about as you consider your next play and your next set of parlays as well. Let\u2019s look at the Tuesday card. LWOS has our best bet for three matches. Post your best bets and thoughts in the comments.<\/span><\/p>\n

WTA Wimbledon<\/b><\/h2>\n

Sakkari \u2013 Tauson: 6:00 EST<\/b><\/h4>\n

H2H: 0-1<\/b><\/p>\n

Maria Sakkari was once a top-five player on the WTA Tour. She suffered some very tough losses several years ago and missed some big chances to win big tournaments. She is trying to regroup and build back her career, but she is struggling. She is 11-13 in 24 pro matches in 2026. She is 0-2 on grass. What could help her here in the <\/span>WTA<\/span> Wimbledon first round is that<\/span><\/a> her opponent, Clara Tauson, has also struggled this year, going 10-14 in 24 pro matches, only 2-3 on grass in five matches. Tauson is ranked No. 25 and has shown in the past that she can compete with the world\u2019s best, but injuries have hampered her a lot in 2026. She needs to be healthy to create some<\/span> WTA Wimbledon excitement for herself.<\/span><\/a>\u00a0<\/span><\/p>\n

Best Bet to Make<\/b><\/p>\n

The over 2.5 set bet is something you could definitely try here, given that Tauson, the clear moneyline favorite according to the betting markets, has been dealing with injuries in an up-and-down season. It\u2019s very realistic to predict a long and difficult three-set match, since neither player is in great form and there is a real question as to which player will win outright. However, because Tauson has been so uncertain in 2026 with her lack of steady health, it seems that Sakkari winning one set is highly probable and the best starting place for your betting strategy. Make Sakkari plus 1.5 sets your main bet and then sprinkle in a smaller wager on over 2.5 sets. If you want to go Sakkari moneyline, a small sprinkle there is also a possibility.<\/span><\/p>\n

That being said, <\/span>betting on Sakkari +1.5 sets is a value bet for sure.<\/b><\/p>\n

Value bet\/ the best odds: Sakkari +1.5 sets @1.64 @unibet<\/b><\/p>\n

Kalinina \u2013 Rakhimova: Time 6:00 EST<\/b><\/h4>\n

H2H: 2-0<\/b><\/p>\n

Anhelina Kalinina had a great clay tennis season, piling up a lot of wins to push her world ranking into the top 70. Now she moves to grass and hopes to at least win a few WTA Wimbledon matches to continue moving her world ranking in the right direction. Kalinina, ranked No. 66, faces Kamilla Rakhimova, ranked No. 70. This matchup is very even on paper, and it only feels more even when you realize that both players have won two matches on grass in 2026. There is not a large amount of daylight between these two players, either overall or on grass. However, Kalinina, because of all the winning she did on clay, is the more in-form player in 2026 and a clear favorite according to the betting markets.<\/span><\/p>\n

<\/p>\n

Best Bet to Make<\/b><\/p>\n

The fact that Kalinina won 30 matches on clay in the first half of 2026, whereas Rakhimova won only two, makes Kalinina the very reasonable betting-market favorite. However, this is grass, a different surface. Kalinina\u2019s grass record is not terrible, but it certainly isn\u2019t elite, either. She is getting a lot of respect for a grass-court match at WTA Wimbledon, given her clay-court results and performance. We think this is a much more even matchup than the markets have, and therefore we think it will go three sets. The over 2.5 set bet fits very nicely for this match, because it figures to be a real battle.\u00a0\u00a0<\/span><\/p>\n

That being said, <\/span>betting on winning 2.5 sets is a value bet for sure.<\/b><\/p>\n

Value bet\/ the best odds: winning 2.5 sets @2.42 @betsson<\/b><\/p>\n

Paolini \u2013 Montgomery: Time 6:00 EST<\/b><\/h4>\n

H2H: 0-0<\/b><\/p>\n

Jasmine Paolini has had a horrible 2026 tennis season. The former WTA Wimbledon runner-up who reached the top five a few years ago has slid out of the top 10 with a series of bad results. She also picked up a foot injury at Roland-Garros and therefore played only one grass match before coming to this tournament. She lost that match. She goes up against an opponent, Robin Montgomery, who has won 10 grass matches this season. Montgomery won Hertogenbosch, her first WTA Tour title, and then won three straight matches in WTA Wimbledon qualifying to get into the main draw. She is on a roll, and it\u2019s easy to see why she is the betting-market favorite against a player who is still ranked in the WTA top 20.<\/span><\/p>\n

Best Bet to Make<\/b><\/p>\n

Montgomery should be favored, and if Paolini\u2019s foot injury hasn\u2019t fully recovered, it\u2019s pretty obvious that Montgomery will advance to the second round of this WTA Wimbledon tournament. However, if Paolini is reasonably healthy and can move fairly normally around the court, she is a good grass tennis player. She made the Wimbledon final two years ago. She is a skilled all-court player who can come to the net and win points there. We don\u2019t think Paolini will win, but we do think Paolini can win a set. Ultimately, this looks and feels like a match that will go to a third set, so the over 2.5 set bet fits well in this spot.\u00a0<\/span><\/p>\n

That being said, <\/span>betting on over 2.5 sets is a value bet for sure.<\/b><\/p>\n

Value bet\/ the best odds: over 2.5 sets @2.45 @unibet<\/b><\/p>\n

Main Photo Credit: Susan Mullane-USA TODAY Sports \u00a0 <\/span><\/i><\/p>\n","protected":false},"excerpt":{"rendered":"

WTA Wimbledon first-round play continues on Tuesday. Whereas the other three major tennis tournaments play their first round over three days, Wimbledon does it in only two. Wimbledon doesn\u2019t play main-draw tennis on a first Sunday. The tournament actually modernized in recent years by having play on the so-called \u201cMiddle Sunday.\u201d The two-day first round […]<\/p>\n","protected":false},"author":5481,"featured_media":68216,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"_lmt_disableupdate":"no","_lmt_disable":"","sfio_featured_image":false,"sfio_embed_code":"","_ef_editorial_meta_date_first-draft-date":"","_ef_editorial_meta_paragraph_assignment":"","_ef_editorial_meta_checkbox_needs-photo":"","_ef_editorial_meta_number_word-count":"","footnotes":""},"categories":[17400,6,4],"tags":[43866,43885,17399,11133,5319,12545,305,11908,43084],"class_list":["post-107732","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-best-bets","category-wimbledon","category-wta","tag-2026-wta-wimbledon","tag-anghelina-kalinina","tag-best-bets","tag-clara-tauson","tag-jasmine-paolini","tag-kamilla-rakhimova","tag-maria-sakkari","tag-robin-montgomery","tag-wta-wimbledon"],"modified_by":"Kane Webb","_links":{"self":[{"href":"https:\/\/lastwordonsports.com\/tennis\/wp-json\/wp\/v2\/posts\/107732","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/lastwordonsports.com\/tennis\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/lastwordonsports.com\/tennis\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/lastwordonsports.com\/tennis\/wp-json\/wp\/v2\/users\/5481"}],"replies":[{"embeddable":true,"href":"https:\/\/lastwordonsports.com\/tennis\/wp-json\/wp\/v2\/comments?post=107732"}],"version-history":[{"count":2,"href":"https:\/\/lastwordonsports.com\/tennis\/wp-json\/wp\/v2\/posts\/107732\/revisions"}],"predecessor-version":[{"id":107739,"href":"https:\/\/lastwordonsports.com\/tennis\/wp-json\/wp\/v2\/posts\/107732\/revisions\/107739"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/lastwordonsports.com\/tennis\/wp-json\/wp\/v2\/media\/68216"}],"wp:attachment":[{"href":"https:\/\/lastwordonsports.com\/tennis\/wp-json\/wp\/v2\/media?parent=107732"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/lastwordonsports.com\/tennis\/wp-json\/wp\/v2\/categories?post=107732"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/lastwordonsports.com\/tennis\/wp-json\/wp\/v2\/tags?post=107732"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}