{"id":107142,"date":"2026-06-21T23:48:28","date_gmt":"2026-06-22T03:48:28","guid":{"rendered":"https:\/\/lastwordonsports.com\/tennis\/?p=107142"},"modified":"2026-06-21T23:48:28","modified_gmt":"2026-06-22T03:48:28","slug":"wta-eastbourne-kessler-kasatkina","status":"publish","type":"post","link":"https:\/\/lastwordonsports.com\/tennis\/2026\/06\/21\/wta-eastbourne-kessler-kasatkina\/","title":{"rendered":"WTA Eastbourne First Round Best Bets Including McCartney Kessler vs Daria Kasatkina"},"content":{"rendered":"

The <\/span>WTA Eastbourne first-round<\/span><\/a> play unfolds on Monday. It\u2019s the week before <\/span>Wimbledon begins<\/span><\/a>, so this tournament is a final chance for WTA professionals to get some match play on grass and sharpen their games heading into the All-England Club. Players who made deep runs at tournaments over the previous two weeks of lawn tennis don\u2019t need to pile up more matches. This week is for the players who don\u2019t think they have received enough match preparation for the third major tournament of the year and the only grass major championship on the calendar. The points and the prize money matter, but getting matches is what matters most. Players who win early in the week will be able to play later in the week and achieve their main goal in Eastbourne. LWOS has our best bets for three matches. Post your best bets and thoughts in the comments..<\/span><\/p>\n

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

Klugman \u2013 Valentova: Time 5:00 EST<\/b><\/h4>\n

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

Hannah Klugman faces Tereza Valentova in Eastbourne. Hannah Klugman could be the face of the future in British tennis. The 17-year-old is just starting off on tour. She got her first WTA Tour main draw win last week in the Nottingham qualifying rounds against Anastasia Zakharova. She didn\u2019t get through the qualifiers, but she got into the main draw as a lucky loser and scored a second win by beating fellow Brit Harriet Dart. Klugman is learning about life on tour, and it will be exciting to see what she can do this summer. Tereza Valentova did not play any matches since the French Open until playing Marie Bouzkova in Nottingham. Bouzkova had a great week in Nottingham, reaching the final, so Valentova had the misfortune of going up against a hot opponent. Valentova will try to regroup here against a teenage foe.<\/span><\/p>\n

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

There is a lot of hype surrounding Hannah Klugman, and she has to feel very confident about getting two WTA Tour wins so early in her professional career. However, Klugman is still just 2-4 on grass in six matches this month. She is losing more often than winning, as one would expect of a 17-year-old who is just getting started. Klugman plus 1.5 sets versus Valentova in straight sets seems to be the choice bettors need to make. We are going to go with Valentova just because the laws of averages suggest that 17-year-olds who are not amazingly talented will usually lose, probably decisively. If Valentova wins the first set, she will probably win the second.\u00a0\u00a0<\/span><\/p>\n

That being said, <\/span>betting on Valentova winning 2:0 is a value bet for sure.<\/b><\/p>\n

Value bet\/ the best odds: Valentova winning 2:0 @1.69 @1xBet<\/b><\/p>\n

Gibson \u2013 Keys: Time 5:00 EST<\/b><\/h4>\n

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

Our next match in the Eastbourne first round is Talia Gibson vs Madison Keys. Gibson had a solid week last week, making the Nottingham quarterfinals by winning multiple matches. She beat Qinwen Zheng, an accomplished player (former WTA top 10), to get to the quarterfinals before she lost to Karolina Pliskova. Madison Keys lost in Berlin last week, falling in the quarterfinals to Jessica Pegula. Before losing to Pegula, though, Keys beat Karolina Muchova in the Round of 16, a very solid win. There\u2019s no shame in losing to Pegula, who beat Aryna Sabalenka this past Saturday to make the Berlin final. Keys hopes that by playing top competition, she will be sharper for this match and for Wimbledon next week.\u00a0\u00a0<\/span><\/p>\n

<\/p>\n

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

There is zero question that Madison Keys is a better and more proven tennis player than Talia Gibson. Even though Gibson had a good tournament last week, she did not play the same caliber of opponent Madison Keys did. Keys also played in-form opponents such as Pegula. Gibson did beat Qinwen Zheng, but Zheng is not playing nearly as well now as she did a few years ago. Keys should absolutely win this match, but you won\u2019t get a great price for Keys moneyline. You would need to bet on the set or game spread to get more value on a Keys bet. The set spread, winning in straight sets, works just fine.\u00a0<\/span><\/p>\n

That being said, <\/span>betting on Keys winning 2:0 is a value bet for sure.<\/b><\/p>\n

Value bet\/ the best odds: Keys winning 2:0 @1.77 @1xBet<\/b><\/p>\n

Kessler \u2013 Kasatkina: Time 5:00 EST<\/b><\/h4>\n

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

McCartney Kessler meets Daria Kasatkina for just the second time. This is a matchup between two players who are both struggling. Both players have played exactly two matches since Roland-Garros, and they are 0-2 in those matches. Neither player has a single grass match victory this month. Losing the first match of a tournament two straight weeks has to negatively affect the confidence of a tennis player, and this is a battle between two players who are in the same basic position. Kessler lost in Queen\u2019s Club while Kasatkina lost in Hertogenbosch. Both players then lost in Nottingham. Which player will be able to bounce back and regroup here in Eastbourne? Which player will remain in a rut?\u00a0<\/span><\/p>\n

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

The reality of this match, in which Kessler is priced as a slight (1.80) favorite on the moneyline, is that neither player deserves your trust as a bettor. When you don\u2019t trust either player (or team) in a sporting competition, the most logical thought is that the competition will be close because neither side is good enough to pull away and win decisively. You could go for the over total games here, but the simplest over the total bet is 2.5 sets. Two struggling players meeting in a match which is expected to be close should produce a three-set match. At the very least, the match should come very close to producing a third set. It feels risky to pick either player on the moneyline, so you might as well predict that the match will go three sets.\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 @2.43 @Betsson<\/b><\/p>\n

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

The WTA Eastbourne first-round play unfolds on Monday. It\u2019s the week before Wimbledon begins, so this tournament is a final chance for WTA professionals to get some match play on grass and sharpen their games heading into the All-England Club. Players who made deep runs at tournaments over the previous two weeks of lawn tennis […]<\/p>\n","protected":false},"author":5481,"featured_media":86395,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"_lmt_disableupdate":"","_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":[5,4],"tags":[43862,17399,416,43055,63,41787,18486,43011,1297],"class_list":["post-107142","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-french-open","category-wta","tag-2026-wta-eastbourne","tag-best-bets","tag-daria-kasatkina","tag-hannah-klugman","tag-madison-keys","tag-mccartney-kessler","tag-talia-gibson","tag-tereza-valentova","tag-wta-eastbourne"],"modified_by":"Kane Webb","_links":{"self":[{"href":"https:\/\/lastwordonsports.com\/tennis\/wp-json\/wp\/v2\/posts\/107142","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=107142"}],"version-history":[{"count":1,"href":"https:\/\/lastwordonsports.com\/tennis\/wp-json\/wp\/v2\/posts\/107142\/revisions"}],"predecessor-version":[{"id":107148,"href":"https:\/\/lastwordonsports.com\/tennis\/wp-json\/wp\/v2\/posts\/107142\/revisions\/107148"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/lastwordonsports.com\/tennis\/wp-json\/wp\/v2\/media\/86395"}],"wp:attachment":[{"href":"https:\/\/lastwordonsports.com\/tennis\/wp-json\/wp\/v2\/media?parent=107142"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/lastwordonsports.com\/tennis\/wp-json\/wp\/v2\/categories?post=107142"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/lastwordonsports.com\/tennis\/wp-json\/wp\/v2\/tags?post=107142"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}