Defending champion:
Roger Federer (2) who defeated Stefanos Tsitsipas (5) 6-4 6-4
Second round results
- Novak Djokovic (1) defeated Philipp Kohlschreiber 6-3 6-1
- Karen Khachanov (7) defeated qualifier Dennis Novak 6-3 6-4
- Gaël Monfils (3) defeated qualifier Yasutaka Uchiyama 6-1 6-2
- Richard Gasquet defeated Benoit Paire (8) 6-4 6-4
- Andrey Rublev (6) defeated Filip Krajinovic 7-6(3) 6-0
- Daniel Evans defeated Pierre-Hugues Herbert 7-5 3-6 7-6(7)
- Jan-Lennard Struff defeated Nikoloz Basilashvili 6-1 6-0
- Stefanos Tsitsipas (2) defeated Alexander Bublik 7-6(1) 6-4
Quarter final match ups
Novak Djokovic (1) v Karen Khachanov (7)
Gaël Monfils (3) v Richard Gasquet
Andrey Rublev (6) v Daniel Evans
Jan-Lennard Struff v Stefanos Tsitsipas (2)
Defending champion:
This tournament was originally held in Santiago in 1993. It shifted location to Viña del Mar for two stretches, 2001-2009 and 2012-2014. It folded after 2014, but 2020 sees its revival and back at Santiago.
Second round results
- Qualifier Renzo Olivo defeated Pablo Cuevas (4) 5-7 7-6(5) 7-6(8)
- Hugo Dellien (6) defeated wildcard Marcelo Tomas Barrios Vera 6-3 7-6(2)
- Federico Delbonis (7) defeated Salvatore Caruso 7-6(1) 6-3
- Casper Ruud (2) defeated wildcard Alejandro Tabilo 6-4 7-5
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