A trio of #NextGenATP leaders qualified for the Next Gen ATP Finals on Wednesday. Canada’s Denis Shapovalov, Aussie Alex de Minaur and Frances Tiafoe of the U.S. joined Greece’s Stefanos Tsitsipas and German Alexander Zverev as players to have qualified for the prestigious 21-and-under event, to be held 6-10 November in Milan. (Zverev will not be playing in Milan because of his Nitto ATP Finals qualification.)

The 19-year-old Shapovalov qualified for the second consecutive year. He fell just short of reaching the semi-finals at the Fiera Milano last year after a breakout season that saw him become the youngest ATP World Tour Masters 1000 semi-finalist in history (since 1990).

The left-hander has backed up his 2017. He made another Masters 1000 semi-final in Madrid, becoming the youngest semi-finalist in tournament history. Shapovalov also reached the semi-finals at the Delray Beach Open and the Rakuten Japan Open Tennis Championships 2018 in Tokyo.

De Minaur’s 2018 rise, however, might be the most drastic of anyone on the ATP World Tour. In December, the #NextGenATP Aussie was No. 210 in the ATP Rankings. This week, the 19-year-old reached a career-high No. 31 and could be even higher when he heads to Milan, as he’s defending only 30 points the remainder of the regular season.

De Minaur, then 18, started the year by making the semi-finals at the Brisbane International (l. to Harrison) and the final at the Sydney International (l. to Medvedev). He was the youngest player to reach semi-finals in consecutive weeks since Rafael Nadal at the 2005 Rolex Monte-Carlo Masters and Barcelona Open Banc Sabadell.

In August, the 19-year-old De Minaur became the youngest Citi Open finalist since Andy Murray in 2006. De Minaur fell to Zverev in the Washington final, which was the youngest ATP World Tour title match since Rafael Nadal, 20, and Novak Djokovic, 19, at the 2007 BNP Paribas Open in Indian Wells.

Watch: Hewitt & De Minaur: A Perfect Combination

Tiafoe reached two ATP World Tour finals and jumped more than 60 spots in the ATP Rankings this year, from No. 108 in January to No. 45 this week.

In February, the 20-year-old won his maiden ATP World Tour title in Delray Beach, beating Juan Martin del Potro, 2017 Next Gen ATP Finals titlist Hyeon Chung, Shapovalov and German Peter Gojowczyk.

Tiafoe became the first wild-card recipient to win the title in the tournament’s 26-year history, and he became the youngest American champion on tour since Andy Roddick, 19, at 2002 Houston.

In May, on the Estoril clay, Tiafoe reached his second ATP World Tour final, falling to home favourite Joao Sousa.

Eight of the world’s best 21-and-under players will compete at the Next Gen ATP Finals. The top seven spots will be determined by the ATP Race To Milan, which ends 29 October, while the eighth spot will be reserved for the winner of an all-Italian qualifier tournament to be held just prior to the Next Gen ATP Finals.

Nick Kyrgios got back to winning ways on Tuesday, defeating home favourite Andrey Rublev 6-3, 4-6, 6-4 at the VTB Kremlin Cup in Moscow.

The fifth-seeded wild card, who suffered early exits in Tokyo and Shanghai, fired 25 aces and regularly impressed the Russian crowd with his shotmaking abilities en route to an 87-minute victory. The 23-year-old improves to 25-13 this season after denying Rublev a first victory in four appearances at the ATP World Tour 250 tournament.

Kyrgios will face Mirza Basic for a place in the quarter-finals. Earlier in the day, Basic overcame Malek Jaziri of Tunisia 7-6(4), 6-2. World No. 37 Kyrgios and Basic have never met at tour level.

Belarusian qualifier Egor Gerasimov struck 12 aces and lost just nine of his first-service points (36/45) in a 6-1, 6-7(5), 6-2 victory over defending champion Damir Dzumhur, the sixth seed from Bosnia and Herzegovina. He will next challenge Frenchman Benoit Paire, who overcame Mischa Zverev of Germany 7-6(6), 2-6, 6-1.

Andreas Seppi notched his third victory over Martin Klizan in four FedEx ATP Head2Head meetings, upsetting the eighth seed 6-1, 7-6(6). The Italian will meet Pierre-Hugues Herbert or Kazakh qualifier Alexander Bublik in the second round.

Russian Evgeny Donskoy saved four set points at 5/6, 6/7, 8/9 and 9/10 in the second set tie-break en route to beating 2013 runner-up Mikhail Kukushkin of Kazakhstan 6-4, 7-6(10) in one hour and 52 minutes. Donskoy, the 2015 Moscow semi-finalist, will next play fourth-seeded Serbian Filip Krajinovic.