Matteo Berrettini vs Mariano Navone — R128 — Canadian Open

The marathon came down to break-point conversion. Mariano Navone took 3 of his 5 chances and saved 11 of 12 behind his own serve, while Matteo Berrettini cashed 1 of 12, including 1 of 9 across the opening set alone. A tiebreak bought Berrettini a third set. Navone answered by breaking in game 2 of the decider for 2-0, the set's only break, and protected it behind a serve that dropped just one game in 15 all match. Berrettini, winner of both prior meetings on record, both on clay, won 73% of first-serve points and out-aced him 4-1, yet finished the day down 100 points to 108. Navone converted his second match point 6 hours, 31 minutes in, and moves on at the Canadian Open.