Wawrinka caused the 14th loss of the Bulgarian in 2019.
Record low results for Grigor Dimitrov after another disappointment on the court.
The 34-year-old Wawrinka beat Grigor Dimitrov 6-4, 6-4 on Monday to set up his third meeting with Khachanov, the sixth seed at the Canadian ATP Masters 1000 event.
Grigor Dimitrov achieved his first victory since Roland-Garros, after dramatically overtaking Steve Johnson in the first round of the ATP 250 Hard-court Tournament in Los Cabos, Mexico.
After four consecutive defeats, Dimitrov suffered success after 2 hours and 28 minutes of play, thanks to two won tiebreaks - 7: 6 (4), 4: 6, 7: 6 (5).
He will begin the new week as the 57th rocket in the world, writes NOVA TV.
Grigor Dimitrov retreated with four more positions in the world rankings and will start the new week as the 57th rocket in the world. The best Bulgarian tennis player dropped out last week at the start in Atlanta, where he lost against World No. 405 Kevin King.
Grigor Dimitrov recorded one of the most unexpected losses in his career after being defeated by Kevin King, who is under number 405 in the world rankings with 7: 5, 6: 4 in a match from the first round of the ATP250 series in Atlanta.
For Grigor, this was the first game after Wimbledon's loss at the start of Muthero, but the Bulgarian tennis player was far away from his best game.
The best Bulgarian tennis player Grigor Dimitrov lost three positions in the ATP world rankings, renewed after the end of the Wimbledon tournament.
28-year-old Dimitrov, who dropped into the first round after an unexpected turnaround with 6: 2, 6: 3, 6: 7 (4), 3: 6, 1: 6 against the debutant Corentin Moutet, ranked 52nd in the rankings.
Bulgaria's best tennis player Grigor Dimitrov scored a difficult victory 6-7 (3), 6-4, 4-6, 7-6 (2), 6-3 over Croatian No. 11 seed Marin Cilic and qualified for the third round of Roland Garros tennis tournament. Dimitrov will play for the fourth time in his career in the third round of the French Open where he will face Stan Wawrinka (Switzerland).
Dimitrov lost to Argentine Federico Delbonis Delbonis with 6-1, 4-6, 2-6, reported NOVA TV.
Grigor Dimitrov was eliminated in the first round of the ATP 250 series in Geneva, after losing to Argentine Federico Delbonis with 6-1, 4-6, 2-6. Bulgaria's first rocket started the qualification race where it won two victories, but today he was stopped by the 84th in the world - Delbonis
Bulgaria's best tennis player Grigor Dimitrov climbed one place in the World Tennis Association (ATP) world rankings. Current ranking for Grigor Dimitrov is ATP 47.
The 28-year-old Bulgarian overcame the qualities of the ATP 250 tournament in Geneva Open and tonight will play against Argentine Federico Delbonis in the first round of the main circuit in Switzerland.