2018 champion and 2017 runner-up Daria Kasatkina kicks off her title defence, and bid to reach a hat-trick of Moscow finals, with a first meeting against No.8 seed Dayana Yastremska. Two weeks ago in Beijing, Kasatkina won three consecutive matches to reach the quarterfinals for the first time since her title run here last year; her only previous attempt to defend a title ended in the 2018 Charleston quarterfinals at the hands of eventual champion Julia Goerges.
Last year's finalist Ons Jabeur lost to Veronika Kudermetova 6-3, 6-4 in their only previous meeting, in the first round of 's-Hertogenbosch in June. Both players are coming off semifinal losses in Tianjin last week - Kudermetova to Heather Watson and Jabeur to eventual champion Rebecca Peterson.
Qualifier Kaia Kanepi is 2-0 against Timea Babos, having defeated the Hungarian 7-5, 4-6, 7-6(2) in the second round of Copenhagen 2012 and 6-3, 6-4 in Miami qualifying this year.
No.8 seed Ekaterina Alexandrova has won 22 of her past 26 indoor matches, including a semifinal showing in Linz last week, and is seeking her first victory in Moscow in her main draw debut. The Russian was a 6-4 6-2 winner over qualifier Jana Cepelova the only time they played previously, in the first round of Nurnberg in May.
No.7 seed Maria Sakkari defeated 2014 champion and 2015 runner-up Anastasia Pavlyuchenkova 6-1, 7-5 in their sole prior match, in the first round of Rome this May. Pavlyuchenkova and defending champion Daria Kasatkina are the only previous Moscow winners remaining in the draw, following two-time champion Svetlana Kuznetsova's first-round exit to Karolina Muchova. Sakkari is playing her first match since falling in the third round of the US Open to Ashleigh Barty, having been sidelined since then with a right wrist injury.
Home qualifier Varvara Gracheva is on a 13-match winning streak, having picked up back-to-back ITF W60 titles in Saint-Malo and Valencia in the past month after a successful summer in which the Russian made her WTA main draw debut as a qualifier in Lausanne, and in her next tournament picked up her first WTA main draw win in Washington over Anna Blinkova. Gracheva ended 2018 ranked World No.447 and is now on the brink of cracking the Top 100.
Kristina Mladenovic leads the head-to-head against Yulia Putintseva 3-2, including both of their previous indoor meetings - 6-2, 7-6(5) in the 2014 Limoges 125K quarterfinals and 6-2, 6-7(3), 6-4 in the 2017 St Petersburg final to collect the only WTA singles trophy of her career so far.
2017 semifinalist Natalia Vikhlyantseva was victorious over qualifier Kirsten Flipkens in their only past match, 6-3, 6-3 in Cincinnati qualifying last year.
ORDER OF PLAY (all courts start 11am)
After 2 ATP matches, not before 2.30pm
 Dayana YASTREMSKA (UKR) vs Daria KASATKINA (RUS)
Ons JABEUR (TUN) vs Veronika KUDERMETOVA (RUS)
After 1 ATP match, not before 8pm
Anastasia PAVLYUCHENKOVA (RUS) vs  Maria SAKKARI (GRE)
Timea BABOS (HUN) vs [Q] Kaia KANEPI (EST)
Not before 12.30pm
[Q] Kirsten FLIPKENS (BEL) vs Natalia VIKHLYANTSEVA (RUS)
After 2 ATP matches
Kristina MLADENOVIC (FRA) vs Yulia PUTINTSEVA (KAZ)
After 1 ATP match, not before 12.30pm
[Q] Jana CEPELOVA (SVK) vs  Ekaterina ALEXANDROVA (RUS)
Polona HERCOG (SLO) vs Katerina SINIAKOVA (CZE)
[Q] Varvara GRACHEVA (RUS) vs Ajla TOMLJANOVIC (AUS)