Israeli-born teenager Denis Shapovalov, who upset top-seeded Rafael Nadal in Montreal’s Rogers Cup tennis tournament, lost in his semifinal match.

Shapovalov lost Saturday night to fourth-seeded Alexander Zverev of Germany.

Shapovalov, 18, is a Canadian who was born in Tel Aviv to parents who had immigrated from the former Soviet Union. He beat Nadal, the world’s number two-ranked player, 3-6, 6-4, 7-6 (4) on Thursday night.

On Friday, he beat France’s Adrian Mannarino 2-6, 6-3, 6-4 to secure his semifinal spot against Zverev.

Shapovalov is the second youngest player ever to defeat Rafael Nadal since the Spanish champion turned pro in 2001. Earlier in the tournament he upset the 2009 U.S. Open champion Juan Martin Del Potro.

He became the youngest player to reach the tournament’s quarterfinals since Bjorn Borg in 1974 and his world ranking rose from 143 to 66.

Argentine Diego Schwartzman, the world’s top-ranked Jewish player (36), lost on Friday in a quarterfinal meeting against Holland’s Robin Haase, ranked 52.