Shanghai R3 previews and predictions: Khachanov vs. Dimitrov, Tsitsipas vs. Humbert

Third-round action at the Shanghai Masters comes to a close on Monday, with Karen Khachanov and Grigor Dimitrov set for a marquee matchup. Stefanos Tsitsipas and Ugo Humbert are also aiming for a spot in the last 16.

(18) Grigor Dimitrov vs. (13) Karen Khachanov

Dimitrov is surging toward the finish line of the 2023 campaign with a remarkable run of consistency. The 19th-ranked Bulgarian has won multiple matches in eight of his last nine tournaments and he can make it nine out 10 with a victory over Khachanov in round three of the Rolex Shanghai Masters on Monday. Dimitrov improved to 32-18 this season by beating Aleksandar Vukic 6-4, 6-3 to open his week in Shanghai.


Khachanov was sidelined from between the French Open and the U.S. Open because of a back injury. His return has been a mixed bag, with an immediate loss in New York to Michael Mmoh followed by a title in Zhuhai and a first-round exit in Beijing at the hands of Lorenzo Musetti. The world No. 14, who defeated Beibit Zhukayev 7-6(1), 4-6, 6-2 on Saturday, is 0-2 lifetime against Dimitrov–both on indoor hard courts. He fell 7-6(6), 6-3 at the 2020 Vienna event and 4-6, 6-2, 6-0 at the 2021 Paris Masters. Given Dimitrov’s current form, it’s hard to see Khachanov turning the tide.

Pick: Dimitrov in 3

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(4) Stefanos Tsitsipas vs. (32) Ugo Humbert

Tsitsipas and Humbert will be squaring off for the fourth time in their careers and it’s no surprise that the matchup has been a favorable one for the Frenchman. His lefty serve and cross-court forehand plus his strong down-the-line backhand all effectively exploit Tsitsipas’ vulnerable one-handed backhand. Humbert leads the head-to-head series 2-1; he prevailed 7-6(4), 6-7(6), 7-6(3) at the 2020 Paris Masters, won 2-6, 7-6(4), 6-2 at the 2021 Tokyo Olympics, and lost 6-3, 6-7(13), 6-1 a couple of weeks later in Toronto.

Humbert should have a great chance to continue such success. The world No. 34 has reached at least the quarterfinals at four of his last seven tournaments, went 2-1 in Davis Cup competition with wins over Cameron Norrie and Stan Wawrinka, and opened in Shanghai with a three-set victory over Botic van de Zandschulp. Tsitsipas is 4-5 in his last nine matches, with three of those five losses coming to opponents ranked outside the top 100. This has the makings of an upset–but it wouldn’t be a big one.

Pick: Humbert in 3

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