Australia's Nick Kyrgios upset top seed and defending champion Daniil Medvedev of Russia 6-7 (2), 6-4, 6-2 on Wednesday at the National Bank Open.
Medvedev controlled the first-set tiebreaker after each player held serve for the first 12 games. Kyrgios opened the second set with a break and didn't relinquish that advantage before controlling the deciding set.
Earlier, American Tommy Paul pulled off the first big upset of the tournament by dispatching second-seeded Carlos Alcaraz of Spain 6-7 , 7-6 , 6-3. Alcaraz, who was making his Canadian debut, fell to 15-3 in Masters 1000 tournaments this season. It was his first career meeting against Paul, who fought off a match ball in the tiebreaker.
Roberto Bautista Agut, the No. 14 seed from Spain, downed American Jenson Brooksby 7-5, 6-1 and Spain's Pablo Carreno Busta topped Denmark's Holger Rune 6-0, 6-3.
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