Canada’s Brad Gushue lost out on a clutch shot in the extra end by Russia, falling to 5-3 in the men’s curling tournament at the Winter Olympic Games with a 7-6 loss.

Gushue, who won Olympic gold at the 2006 Winter Games in Turin, is third in the standings with one round-robin game remaining. The top four teams advance to the medal round. Great Britain and Sweden have already advanced to the quarterfinals.

Canada’s last game in the round-robin will be a must-win against Great Britain, Wednesday at 8:05 p.m. ET.

Russia, skipped by Sergei Gluhkov, broke a 4-4 deadlock in the ninth end with an impressive shot that knocked out two Canadian stones that left Russia with two. Then Glouhkov stole the game with another clutch shot on the final rock in the extra end to give his rink the win and boost its record to 4-4.

Elsewhere, the U.S. dropped to 4-4 after losing to Italy, and sits behind Canada in fourth.

The Canadian women’s curling team, skipped by Jennifer Jones, has the day off with their next game against the United States, skipped by Tabitha Peterson (Tuesday 8:05 p.m. ET). Jones is tied for fifth in the standings with a 3-3 record.