Cincinnati delivered one of the biggest shocks of the tournament as Novak Djokovic's campaign ended in dramatic fashion against Thiago Tirante. The Argentine's victory was made even more remarkable by the physical struggles that affected Djokovic in the punishing conditions, while Adolfo Daniel Vallejo also produced a major upset by eliminating No. 19 seed Valentin Vacherot in straight sets.
There was no shortage of three-set drama elsewhere, with Alex de Minaur and Jiri Lehecka fighting through deciding-set battles and Rafael Jodar producing another extraordinary comeback against Denis Shapovalov. Tommy Paul also survived a demanding encounter with Hubert Hurkacz, ensuring another packed day of action in Cincinnati.
Vallejo produces major upset against Vacherot
Adolfo Daniel Vallejo 6-3, 6-3 Valentin Vacherot
Adolfo Daniel Vallejo produced one of the biggest surprises of the day by eliminating world No. 19 Valentin Vacherot in straight sets. The young Paraguayan controlled the match from the baseline and consistently exposed the Monaco player's weaknesses on serve, converting three of his three break-point opportunities while never allowing Vacherot to create a break chance of his own.
Vacherot's first serve remained effective, with the Monaco player winning 80% of those points, but his second delivery became a major liability. He won only 33% of second-serve points and committed five double faults, giving Vallejo repeated opportunities to attack. The Paraguayan made the most of them and never allowed Vacherot to build sustained momentum.
The defeat is particularly damaging for Vacherot, who has now lost three consecutive matches, while Vallejo moves into the third round with significant momentum. His reward is another major test against Tommy Paul, giving the youngster an opportunity to follow up his upset with another victory over a seeded opponent.
Valentin Vacherot during his second round match at the 2026 Rolex Monte-Carlo Masters
Tirante stuns Djokovic in brutal Cincinnati battle
Novak Djokovic 6-2, 4-6, 4-6 Thiago Agustin Tirante
Thiago Agustin Tirante produced the biggest result of his career by defeating Novak Djokovic in a dramatic three-set battle, winning 2-6, 6-4, 6-4. The Argentine's victory came in punishing heat and humidity, with Djokovic visibly struggling physically during the second set as the conditions began to take a significant toll.
The most revealing moment came during an extraordinary 18-minute third game of the second set. Djokovic saved four break points across nine deuces, but repeatedly bent over between points and eventually dropped to his hands and knees following one particularly demanding rally. After finally surviving the game, the Serbian took a medical timeout, with both the physiotherapist and doctor attending to him while ice towels were used to help him manage the conditions.
Djokovic nevertheless fought to stay in the contest and made Tirante work for the victory. After the Argentine took the second set, both players went back to the locker room to cool down before returning for the decider. Tirante remained composed when the match resumed and completed one of the biggest upsets of the Cincinnati tournament, potentially ending Djokovic's run in an event that could prove to be his final appearance.
De Minaur survives Halys comeback attempt
Quentin Halys 6-1, 3-6, 6-7 Alex de Minaur
Alex de Minaur had to fight back from a disastrous start before eventually overcoming Quentin Halys in a deciding-set tiebreak. The Australian found himself two breaks down almost immediately and had few answers to Halys' aggressive tennis, allowing the Frenchman to cruise through the opening set 6-1.
De Minaur gradually changed the direction of the match in the second set. He began matching Halys' intensity from the baseline, survived several break-point opportunities and eventually found the breakthrough he needed late in the set. Once he secured the break, the Australian held his nerve on serve to level the match and force a decider.
The third set became a much tighter contest, with both players saving multiple break points and refusing to give away an opening. Halys repeatedly escaped danger on serve, but De Minaur continued to look more threatening in the important exchanges. The Australian ultimately prevailed in the tiebreak to complete the comeback and avoid what would have been a major upset.
Paul survives Hurkacz in three-set battle
Tommy Paul 6-4, 6-7, 6-3 Hubert Hurkacz
Tommy Paul survived a demanding three-set encounter with Hubert Hurkacz to secure his place in the next round. The American had to navigate the Polish player's powerful serve and the pressure of a closely contested second set, but ultimately found another level in the deciding set to claim the victory 6-4, 6-7, 6-3.
Hurkacz's ability to keep the match tight behind his delivery made it difficult for Paul to pull away, and the Polish player responded after losing the opening set by forcing a tiebreak in the second. Paul, however, remained composed after losing that crucial set and regained control when the match entered its decisive phase.
Lehecka edges Berrettini in another three-set test
Jiri Lehecka 6-4, 6-7, 6-3 Matteo Berrettini
Jiri Lehecka won one of the day's most competitive battles, defeating Matteo Berrettini in three sets after more than two hours of high-level tennis. Both players were highly effective behind their first serves, approaching 80% of points won on first delivery, but Lehecka proved more efficient when opportunities appeared.
The Czech converted two of six break points, while Berrettini failed to take any of his four opportunities. That difference ultimately proved decisive, particularly after Berrettini narrowly claimed the second-set tiebreak to level the match. Lehecka responded strongly in the decider and used his serve to prevent the Italian from building another comeback.
Berrettini's inability to capitalize on his break chances proved costly, while Lehecka's consistency in the crucial moments allowed him to close out the 6-4, 6-7, 6-3 victory. The Czech continues his Cincinnati campaign after another strong performance against a dangerous opponent.
Jodar completes stunning comeback against Shapovalov
Rafael Jodar 7-5, 4-6, 7-5 Denis Shapovalov
Rafael Jodar produced another remarkable comeback in Cincinnati, recovering from 1-5 down in the deciding set to defeat Denis Shapovalov 7-5, 4-6, 7-5. The Spaniard once again showed his ability to thrive in long, physical battles, refusing to concede even when Shapovalov appeared to have the match completely under control.
Jodar had already fought his way back from a break down in the opening set, recovering the deficit at 5-5 before finding another break late in the set to move ahead. Shapovalov responded in the second, taking an early break and this time managing to protect his advantage under pressure to level the match.
The deciding set appeared to belong entirely to Shapovalov when the Canadian moved 5-1 ahead with a double break. But Jodar refused to surrender, saving two match points before embarking on an extraordinary six-game winning streak. The Spaniard turned the match around completely, eventually closing out the 7-5, 4-6, 7-5 victory and advancing to the third round in Cincinnati.
Rafael Jodar of Spain during the Mutua Madrid Open 2026