MONTREAL — Canada's Frank Dancevic failed to advance to the Rogers Cup main draw on Sunday after falling 7-6(1), 2-6, 2-6 to American Tim Smyczek.
The match, played at Uniprix Stadium, took two hours to complete.
Dancevic, from Niagara Falls, Ont., converted just 1 of 6 break points while Smyczek broke the Canadian five times.
Dancevic, 32, did have seven aces but it wasn't enough to get past the tournament's 13th ranked qualifier.
Milos Raonic, Denis Shapovalov, Brayden Schnur, Vasek Pospisil and Peter Polansky are the Canadians in the tournament's main draw.
Vancouver's Pospisil faces Toronto's Polansky in first round play on Monday while Schnur, of Toronto, is also in action against France's Richard Gasquet. Raonic, a Thornhill, Ont., product received a first round bye as the tournament's No. 6 seed while Shapovalov of Richmond Hill, Ont., faces Brazil's Rogerio Dutra Silva on Tuesday.
France's Pierre-Hugues Herbert, the No. 1 ranked qualifier, recovered from a poor second set for a 6-2, 2-6, 6-3 win over Russian Mikhail Youzhny.
In other second-round qualifiers, American Reilly Opelka upset compatriot Ernesto Escobedo 6-2, 6-3, Nobert Gombos of Slovakia beat Ireland's James McGee 6-4, 6-4, Italy's Thomas Fabbiano downed Nicolas Mahut of France 6-2, 7-5, France's Vincent Millot edged Brydan Klein of Britain 7-6(3), 7-6(4) and Dudi Sela of Israel got past Australia's Matthew Ebden 6-3, 7-6(7).