Jil Teichmann (WTA 38) ha iniziato nel migliore dei modi il proprio cammino nel WTA 500 di Chicago. La 24enne ha infatti battuto Kaia Kanepi (66) con il punteggio di 7-6 (7/3) 7-5, qualificandosi per i sedicesimi di finale, dove affronterà la polacca Magda Linette (54). Contro l'estone la mancina rossocrociata si è portata velocemente sul 5-0 nel primo set, subendo però il ritorno dell'avversaria che, da lì in poi, ha giocato un match alla pari. Teichmann ha poi chiuso su proprio servizio al primo match point dopo 1h44'.
Viktorija Golubic (46) ha invece dovuto salutare subito l'Illinois. La zurighese è stata superata da Amanda Anisimova (82), che davanti al pubblico di casa si è imposta per 6-0 5-7 6-4. Bucata clamorosamente l'entrata in materia, la 28enne ha cercato di rimettersi in carreggiata contro la 20enne statunitense disputando una buona seconda frazione. Sotto 0-4 nel terzo set è poi riuscita a rimontare soltanto un break, concedendo la vittoria all'avversaria al termine di un match durato poco più di due ore.
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