Andrey Rublev became the second teenager to make the third round when he stunned Bulgarian seventh seed Grigor Dimitrov 7-5, 7-6(3), 6-3.
Rublev, just 19 and the world No 53, joins 18-year-old Denis Shapovalov of Canada in the last-32 at a Grand Slam event for the first time.
“It’s an amazing feeling. I’m very happy to win this match,” said Rublev after stunning Cincinnati Masters champion Dimitrov.
However, 19-year-old Taylor Fritz of the United States was unable to join Rublev and Shapovalov in the next round when he lost 6-4, 6-4, 4-6, 7-5 to Austrian sixth seed Dominic Thiem.
Thiem saved 16 of 18 break points he faced in a stalwart defensive display.
Also going through to the last-32 was 2009 champion Juan Martín Del Potro, the 24th seeded Argentine, who saw off Spanish qualifier Adrian Menendez-Maceiras 6-2, 6-3, 7-6(3).
Top seed Rafael Nadal, the 2010 and 2013 champion, faces Japan’s Taro Daniel, the New York-born world No 121 in the night session.
Belgian ninth seed David Goffin saw off Guido Pella of Argentina 3-6, 7-6(5), 6-7(2), 7-6(4), 6-3 in a marathon four-hour-12-minute match.
He will face French 18th seed Gael Monfils, a semi-finalist last year, who downed Donald Young of the United States 6-3, 6-7(3), 6-4, 2-6, 7-5.
Women play longest match
A record was set when American Shelby Rogers and 25th-seeded Australian Daria Gavrilova played out the longest ever women’s singles match.
Their three-hour-33-minute clash saw Rogers win 7-6(6), 4-6, 7-6(5) on a fifth match point in a final set that lasted 90 minutes.
Their second-round tie on Court 10 went past the previous longest of the three hours and 23 minutes it took Johanna Konta to beat Garbine Muguruza in the second round two years ago.
Karolina Pliskova had to battle back from a set down to make the last-32 and hang on to her world No 1 spot.
The Czech player, who was runner-up in 2016, downed American qualifier Nicole Gibbs 2-6, 6-3, 6-4.
She was joined in the third round by fourth seed Elina Svitolina, one of the pretenders to her top ranking, and French Open champion Jelena Ostapenko.
“It’s easier for the other girls to play me as there is more pressure being number one,” said Pliskova who would have lost top spot had she lost.
Ukraine’s Svitolina reached the last-32 for a third successive year by breezing past Russia’s Evgeniya Rodina 6-4, 6-4.
Ostapenko, the 12th-seeded Latvian, made the third round for the first time with a 6-4, 6-4 win against Romania’s Sorana Cirstea.
Japan’s Naomi Osaka, just 19, followed up her win over defending champion Angelique Kerber with a 6-3, 4-6, 7-5 win over Denisa Allertova of the Czech Republic.