After a dramatic Day 2 which saw two matches decided in final-set tie-breaks at the Intesa Sanpaolo Next Gen ATP Finals, Thursday’s play promises more thrills, with three semi-final places still up for grabs in Milan.
Lorenzo Musetti and Jack Draper will close round-robin play with a winner-takes-all showdown in the Red Group, where the undefeated Dominic Stricker has already clinched first place. Brandon Nakashima is also a perfect 2-0, but could still be pipped by Jiri Lehecka and Francesco Passaro in the Green Group for a place in the semis. Matteo Arnaldi also has a potential path into the knockout rounds.
With several qualifying scenarios in play, a high-stakes day of tennis is on tap at the Allianz Cloud.
 Lorenzo Musetti (ITA) vs.  Jack Draper (GBR)
No need for any computations here! This marquee matchup between the two highest-ranked players in the Milan field effectively amounts to a traditional quarter-final: The winner is through to the semis while the loser will head home for the offseason.
The first ATP Head2Head meeting between Musetti and Draper is a rematch of their 2019 Wimbledon juniors quarter-final, which Draper won on home soil en route to the final. This time it will be the Italian with home advantage, though he will have to overcome disappointment and fatigue from a late-night, five-set defeat to Stricker on Tuesday.
Draper enters Day 3 on the heels of his first Milan victory, a 1-4, 4-2, 4-3(2), 4-2 result against Chun-Hsin Tseng which eliminated the sixth seed from semi-final contention. After losing the opening set for the second straight match, the Briton used a mid-set pep talk to turn the tables.
“It’s a quick format, so you need to be sharp,” he said post-match. “When I sat down for the change of ends at the end of the first set, I had a real go at myself. I said, ‘You’ve got to be sharper, you’ve got to be more switched on and you’ve got to be alert out here’, because it can go very quickly if you’re not quite all there. So, I’m glad I mentally turned things round.”
A quick start could prove critical in quieting the Milan crowd, who have roared in support of the three Italian players competing this week.
 Brandon Nakashima (USA) vs.  Francesco Passaro (ITA)
Despite his perfect 2-0 record, Nakashima may still need a result in his final match to reach the semi-finals. But a win for Arnaldi against Lehecka would take the drama out of this match — at least for the American, who would be assured of a semi-final place in that scenario.
In all likelihood, only a heavy defeat would put Nakashima in danger of a shock exit. After two days of play, the fourth seed matches Stricker with a tournament-best 6-2 set record, but holds a better games-won percentage than the Swiss after wins against Arnaldi and Lehecka.
Passaro, who saved three match points to defeat fellow Italian Arnaldi on Wednesday, currently sits third in the Green Group but could still finish top if he follows an Arnaldi win with a victory of his own on Day 3.
 Jiri Lehecka (CZE) vs.  Matteo Arnaldi [ITA]
Lehecka, thanks to his straight-sets win against Passaro on Tuesday, is in second place in the Green Group. A victory in three or four sets against Arnaldi would clinch his progress to the semi-finals, though a five-set win could leave him in danger of elimination by percentage of games won — provided Passaro scores a straight-sets victory against Nakashima.
For Arnaldi, there is only one path to the semi-finals. The Italian must defeat Lehecka in Thursday’s opening match and receive help from Nakashima with a win against Lehecka. In that scenario, Nakashima would win the group, with Arnaldi moving into second.
 Chun-Hsin Tseng (TPE) vs.  Dominic Stricker (SUI)
Stricker earned his semi-final berth the hard way by completing an upset double against Draper and Musetti, the two highest-ranked men in the field. All eight of the sets contested by the Swiss have been decided in tie-breaks as he beat Draper in three and Musetti in five.
While Stricker cannot be knocked off his perch atop the Red Group, Tseng will be motivated to finish his Milan campaign on a high note after two straight-sets defeats. The 21-year-old is the second Asian man to compete at the Intesa Sanpaolo Next Gen ATP Finals, following 2017 champ Hyeon Chung.