Paolo Lorenzi of Italy opened up main draw action on Monday at the New York Open by scoring the first upset of the tournament, earning a marathon 7-6(4), 6-7(4), 6-4 win over No. 8 seed Tennys Sandgren of the United States.

Both players won 106 points on the day, but it was the Italian who prevailed in the most crucial moments. He scored the lone break of the match at 1-1 in the final set and rode the momentum to victory after two hours and 32 minutes.

The win gives the 37-year-old his first main draw victory since the 2018 US Open. He has primarily competed on the ATP Challenger Tour over the past six months, but qualified for the main draw this year at ATP Tour events in Doha and Cordoba.

Next up for Lorenzi is the winner between Ryan Harrison of the United States and Peter Polansky of Canada.

Bernard Tomic also picked up his first ATP Tour main draw win of 2019 with a convincing 6-4, 6-2 victory over Lukas Lacko in just 53 minutes. The Aussie will next face top seed John Isner.

The final singles match on Monday’s schedule features No. 7 seed Jordan Thompson of Australia taking on wild card and hometown favourite Noah Rubin.

Germany’s Maximilian Marterer will try to do what no man has done before at the Argentina Open: beat Dominic Thiem. The left-hander secured a second-round meeting with Thiem after dismissing local qualifier Facundo Bagnis 6-4, 6-2 on Monday evening in Buenos Aires.

Marterer broke in the third game and sailed the rest of the way, never facing a break point against the 28-year-old, No. 148 in the ATP Rankings. Thiem and Marterer faced off at the Gerry Weber Open in Halle in 2017, a 7-5, 6-3 win for Thiem. The top-seeded Austrian is 9-0 in his two appearances in the Argentine capital, including a semi-final win over Rafael Nadal in 2016.

Elsewhere on Monday, Italian qualifier Lorenzo Sonego upset sixth seed Nicolas Jarry, the 2018 Brasil Open finalist, 6-7(3), 6-4, 6-3. Sonego, 23, will play Spain’s Roberto Carballes Baena or Taro Daniel of Japan for a place in the quarter-finals.

Christian Garin of Chile rallied from down a set and a break to outlast #NextGenATP Canadian Felix Auger-Aliassime 3-6, 7-5, 6-3. His reward is a battle with third seed Marco Cecchinato of Italy in the second round. Fittingly, their only previous meeting came four years ago in the qualifying rounds at Buenos Aires, a match won by the Italian in straight sets.

Spaniard Albert Ramos-Vinolas, 2017 Rolex Monte-Carlo Masters finalist (l. to Nadal), ended Brazilian Rogerio Dutra Silva’s run 6-3, 6-4. Ramos-Vinolas will meet either countryman David Ferrer or eighth seed Malek Jaziri.

Stan Wawrinka got the better of his good friend Benoit Paire in a match of power-hitting on Monday night at the ABN AMRO World Tennis Tournament in Rotterdam.

“It was difficult to play against a good friend and we played some good shots. Winning the first set was the key and I played with confidence in the second set,” said Wawrinka. “Being back in Rotterdam is great. There is a great atmosphere here and [tournament director] Richard Krajicek is doing a great job to keep improving the tournament.”

Wawrinka, the 2015 champion, was ultimately more consistent, saving three set points in the first set en route to a 7-6(4), 6-1 victory in 71 minutes. He will next face fourth-seeded Canadian Milos Raonic or Philipp Kohlschreiber of Germany.

“I feel good in general. I had a good off-season and took the time to get back in shape,” said Wawrinka. “I now need matches to build my confidence, but I have to be patient with that. It was a long year to get back physically, but now I’m playing well.”

Paire broke serve for a 4-3 advantage, courtesy of consecutive groundstroke errors from Wawrinka, but the Swiss wild card saved a set point with an ace two games later at 30/40. Two further opportunities went begging for Paire on serve at 5-4 — a backhand error, and a clever play by Wawrinka that opened up the court for a winner.

In the tie-break, Wawrinka stepped inside the baseline to gain the momentum. After losing the opening game of the second set, he won the next six games to close out the match.

Monday’s evening session also saw No. 9 seed Nikoloz Basilashvili rally from down a set and a break to defeat Hyeon Chung 4-6, 7-6(1), 6-2. Although the Georgian was unable to serve out the second set at 5-3, he raised his level in the tie-break to even the match. The final set saw Basilashvili go on a five-game run and eventually wrap up the win after two hours and 17 minutes. 

Awaiting Basilashvili in the next round is the winner between Martin Klizan of Hungary and Marton Fucsovics of Hungary, who finished runner-up last week in Sofia (l. to Medvedev).

Other first-round matches on Monday saw Andreas Seppi survive a mid-match surge from qualifier Peter Gojowczyk to prevail 7-6, 3-6, 6-2, while Mikhail Kukushkin didn’t drop serve in his 6-2, 7-6(4) win over home favourite Robin Haase.

Tuesday’s night session features top seed Kei Nishikori of Japan squaring off against Pierre-Hugues Herbert of France, followed by second seed Karen Khachanov of Russia taking on local wild card Tallon Griekspoor. Raonic and Kohlschreiber open up the day session.