NEW YORK - Croatian fifth seed Marin Cilic crashed out and Canadian teen Denis Shapovalov became the youngest man since 1989 into the US Open last 16 in a wild Friday on which absent six-time champion Serena Williams become a mother.

MONTREAL - Canadian teenager Denis Shapovalov shocked top seeded Rafael Nadal to reach the quarter-finals of the ATP Montreal Masters tournament, spoiling the Spaniard's chances of returning to world number one.