MADRID — Montreal’s Gabriel Diallo, who earned entry into the Madrid Open as a lucky loser, advanced to the fourth round Tuesday with a 2-6, 6-4, 6-4 comeback win over Britain’s Cameron Norrie.

The 22-year-old fired eight aces and earned key breaks in each of the final two sets to move on at the clay-court tournament.

Diallo, the last Canadian remaining in Madrid, earned his spot in the main draw as a replacement for Japan’s Yoshihito Nishioka, who withdrew before the tournament. He has reeled off wins over Zizou Bergs, Kamil Majchrzak and Norrie.

He will next face No. 15 seed Grigor Dimitrov of Bulgaria in the round of 16 — his first seeded opponent at the tournament.

It marks the best performance of Diallo’s career at an ATP Masters 1000 event.

Earlier, the 29th-seeded Denis Shapovalov of Richmond Hill, Ont., dropped a 6-3, 7-6 (3) decision to No. 6 Alex de Minaur of Australia.

Shapovalov fired six aces but was undone by five double faults and 37 unforced errors.

“He’s got tremendous firepower from every part of the court, and I had to do my best to neutralize it, and not let him dictate as much as he could,” said De Minaur, who improved to 5-0 against Shapovalov.

Both Diallo’s and Shapovalov’s matches had been postponed from Monday after a mass power outage disrupted large parts of Spain and Portugal.

With files from The Associated Press.

This report by The Canadian Press was first published April 29, 2025.