Arthur Rinderknech continued his fantastic season by defeating Federico Delbonis at the European Open, while Marin Cilic battled through in the Kremlin Cup.
Rinderknech, who sits 65th in the world rankings, had not recorded a Tour-level victory before 2021 but has now triumphed 15 times after cruising past Delbonis 6-4 6-4.
The Frenchman will meet eighth seed Dusan Lajovic in the second round in Antwerp, after the Serbian downed Richard Gasquet 7-6 (7-3) 6-1 on Monday.
The other first-round clash in Belgium saw Alexei Popyrin capitulate in the third set as he succumbed to a 4-6 6-3 0-6 defeat against world number 62 Botic van de Zandschulp.
Americans Jenson Brooksby and Brandon Nakashima also booked their places in the main draw. Brooksby defeated Norbert Gombos 6-4 6-2, while Nakashima overcame Pierre-Hugues Herbert 6-2 6-4.
Meanwhile in Russia, Cilic – who has claimed the crown in Moscow twice previously – recovered from a first-set scare in his round-of-32 tie with qualifier Damir Dzumhur, eventually triumphing 6-7 (4-7) 6-1 6-1.
John Millman experienced similar difficulties, with Benjamin Bonzi claiming the first set before the Australian succeeded 6-7 (5-7) 6-4 6-3 to set up a potential second-round match against fifth seed Alexander Bublik.