Denis Shapovalov ended Rafael Nadal’s Italian Open run.
Shapovalov qualified for the quarterfinals of the Italian Open where he will face Casper Ruud.
Nadal was bidding for an 11th crown at the clay courts of Rome.
The Canadian won 1-6, 7-5, 6-2 avenging last year’s loss to the Spaniard.
The 13th seed advances to his sixth ATP Masters 1000 quarter-final, denying Nadal a landmark 100th trip to that stage at the Masters 1000 level.
After going down an instant break in the final set, Shapovalov won the final five games.
Nadal seemed to struggle with an apparent foot injury a likely recurrence of his chronic left-foot problem.
The one-sided finish misrepresented the hard-fought nature of the contest to that point, with the first two sets seeing a combined 17 breakpoints.
With the French Open around the corner, Nadal has little time to recover.
Novak Djokovic meanwhile moved to within one win of retaining his World No. 1 status.
The Serb overcame Stan Wawrinka 6-2, 6-2, and now leads their head2head 20-6.
Djokovic soaked up Wawrinka’s heavy ball-striking and pulled the former World No. 3 around to advance to the quarter-finals after 75 minutes.
Wawrinka, still recovering from a long injury layoff had his best tournament run in 15 months.
Joining them in the next round also are Stefanos Tsitsipas and Alexander Zverev.
Tsitsipas took care of Karen Khachanov 4-6, 6-0, 6-3.
Alexander Zverev had an easier game again de Minaur, beating the Australian 6-3, 7-6 (7) to reach the Italian Open quarterfinals.
