<p>Nick Kyrgios broke twice in the final set as he rallied to topple world number one Daniil Medvedev in the second round of the ATP Montreal Masters on Wednesday.</p>.<p>Australia's Wimbledon finalist beat Medvedev 6-7 (2/7), 6-4, 6-2 to produce his second career upset of a reigning number one after ambushing Rafael Nadal at Wimbledon in 2014.</p>.<p>Kyrgios produced his usual on-court antics, complaining about a high bounce, hitting a ball into the stands to draw a warning and bickering with his player box in moments of tension.</p>.<p>But after gathering his formidable resources, the 27-year-old ranked 37th finished off the match in exactly two hours.</p>.<p>"This is our fourth meeting and we know each other well," Kyrgios said. "I don't go in looking at the rankings, just the guy in front of me.</p>.<p>"I had a clean objective today -- play a lot of serve and volley and execute better.</p>.<p>"Hopefully I can keep this rolling and keep on winning. Medvedev is a machine -- he's number one for a reason."</p>.<p>Both players were coming off weekend title wins, Kyrgios at the Washington 500 on Sunday and Medvedev at Los Cabos, Mexico, on Saturday.</p>.<p>Kyrgios has won 14 of his last 15 matches to improve to 29-7 for 2022.</p>.<p>Medvedev lost for the 11th time in 2022, but by reaching the final at Los Cabos -- where he lifted his first trophy of the season -- he is assured of taking the number one ranking into his US Open title defense later this month.</p>.<p>He was barred from Wimbledon as the tournament excluded Russian and Belarussian players over Russia's invasion of Ukraine.</p>.<p>Second-seeded Carlos Alcaraz, who like Medvedev enjoyed a first-round bye, fared no better in his opening match.</p>.<p>American Tommy Paul spoiled the Spaniard's Canadian debut with a 6-7 (4/7), 7-6 (9/7), 6-3 victory.</p>.<p>The unseeded American converted his fifth match point to seal the second-round victory in three hours and 20 minutes.</p>.<p>Alcaraz came into the event with two prestige Masters 1000 titles from Miami and Madrid and holding a 42-7 record this season.</p>.<p>But the 34th-ranked Paul claimed victory on a volley winner after holding off the Spaniard's charge from 5-2 down in the third set. The American stayed in the match as he rallied from a 4-1 deficit in the second set to start his comeback surge.</p>.<p>"It was nice to finish this match at the net," said Paul, who fired 36 winners to Alcaraz's 33. "I did a lot of things well today.</p>.<p>"I played a good level of tennis, comfortable tennis. I'm happy to get through and now have to recover for tomorrow."</p>.<p>Fourth seed Casper Ruud backed up his defeat earlier this season of Alex Molcan, beating the Slovakian 7-6 (7/3), 6-3 in just under two hours.</p>.<p>The Norwegian with three trophies so far in 2022 had to work to win the opening set after dropping serve as he tried to close it out leading 5-4.</p>.<p>It eventually took a tiebreaker for Ruud to prevail. He sealed his third-round place in straight sets for his 36th win of the season.</p>.<p>"It's always a tough fight against him," Ruud said.</p>.<p>"He's very fast and can give everyone problems," he added of the player coached by Novak Djokovic's former mentor Marian Vajda.</p>.<p>Elsewhere, Italian Jannik Sinner needed three sets to get past Adrian Mannarino 2-6, 6-4, 6-2 while Alex de Minaur lined up an all-Aussie Thursday match against Kyrgios by defeating Grigor Dimitrov 7-6 (7/4), 7-5.</p>
<p>Nick Kyrgios broke twice in the final set as he rallied to topple world number one Daniil Medvedev in the second round of the ATP Montreal Masters on Wednesday.</p>.<p>Australia's Wimbledon finalist beat Medvedev 6-7 (2/7), 6-4, 6-2 to produce his second career upset of a reigning number one after ambushing Rafael Nadal at Wimbledon in 2014.</p>.<p>Kyrgios produced his usual on-court antics, complaining about a high bounce, hitting a ball into the stands to draw a warning and bickering with his player box in moments of tension.</p>.<p>But after gathering his formidable resources, the 27-year-old ranked 37th finished off the match in exactly two hours.</p>.<p>"This is our fourth meeting and we know each other well," Kyrgios said. "I don't go in looking at the rankings, just the guy in front of me.</p>.<p>"I had a clean objective today -- play a lot of serve and volley and execute better.</p>.<p>"Hopefully I can keep this rolling and keep on winning. Medvedev is a machine -- he's number one for a reason."</p>.<p>Both players were coming off weekend title wins, Kyrgios at the Washington 500 on Sunday and Medvedev at Los Cabos, Mexico, on Saturday.</p>.<p>Kyrgios has won 14 of his last 15 matches to improve to 29-7 for 2022.</p>.<p>Medvedev lost for the 11th time in 2022, but by reaching the final at Los Cabos -- where he lifted his first trophy of the season -- he is assured of taking the number one ranking into his US Open title defense later this month.</p>.<p>He was barred from Wimbledon as the tournament excluded Russian and Belarussian players over Russia's invasion of Ukraine.</p>.<p>Second-seeded Carlos Alcaraz, who like Medvedev enjoyed a first-round bye, fared no better in his opening match.</p>.<p>American Tommy Paul spoiled the Spaniard's Canadian debut with a 6-7 (4/7), 7-6 (9/7), 6-3 victory.</p>.<p>The unseeded American converted his fifth match point to seal the second-round victory in three hours and 20 minutes.</p>.<p>Alcaraz came into the event with two prestige Masters 1000 titles from Miami and Madrid and holding a 42-7 record this season.</p>.<p>But the 34th-ranked Paul claimed victory on a volley winner after holding off the Spaniard's charge from 5-2 down in the third set. The American stayed in the match as he rallied from a 4-1 deficit in the second set to start his comeback surge.</p>.<p>"It was nice to finish this match at the net," said Paul, who fired 36 winners to Alcaraz's 33. "I did a lot of things well today.</p>.<p>"I played a good level of tennis, comfortable tennis. I'm happy to get through and now have to recover for tomorrow."</p>.<p>Fourth seed Casper Ruud backed up his defeat earlier this season of Alex Molcan, beating the Slovakian 7-6 (7/3), 6-3 in just under two hours.</p>.<p>The Norwegian with three trophies so far in 2022 had to work to win the opening set after dropping serve as he tried to close it out leading 5-4.</p>.<p>It eventually took a tiebreaker for Ruud to prevail. He sealed his third-round place in straight sets for his 36th win of the season.</p>.<p>"It's always a tough fight against him," Ruud said.</p>.<p>"He's very fast and can give everyone problems," he added of the player coached by Novak Djokovic's former mentor Marian Vajda.</p>.<p>Elsewhere, Italian Jannik Sinner needed three sets to get past Adrian Mannarino 2-6, 6-4, 6-2 while Alex de Minaur lined up an all-Aussie Thursday match against Kyrgios by defeating Grigor Dimitrov 7-6 (7/4), 7-5.</p>