Russia's Mikhail Youzhny upset 14th seed Marin Cilic of Croatia at the Rogers Cup in Montreal on Monday.
Youzhny beat the 20-year-old 4-6 7-6 (7/4) 6-1 to claim his third win in three meetings with the Croatian after also beating him in India and France last year.
Two of Youzhny's compatriots Igor Andreev and Dmitry Tursunov also met in the first round, with the former progressing after an ankle problem forced Tursunov to quit at 5-5 in the first set. Andreev will now take on Andy Roddick, who received a first-round bye.
France's Jeremy Chardy set up a second-round meeting with Andy Murray after he beat Lu Yen-Hsun of Chinese Taipei 6-7 (5/7) 6-3 6-4.
Frederic Niemeyer gave the Canadian crowd something to cheer as he overcame Russia's Igor Kunitsyn 7-5 6-1. He will now face Roger Federer in the second round.
Thirteenth seed Gael Monfils took three sets to overcome 2000 US Open champion Marat Safin 6-2 3-6 6-2, extending his impressive head-to-head record against the Russian to 4-0.
Stanislas Wawrinka of Switzerland and Germany's Rainer Schuettler each progressed with straight-sets victories over Nicolas Kiefer and Florent Serra respectively.
Ninth seed Gilles Simon hammered home favourite Frank Dancevic 6-1 6-2 in a match lasting an hour.
Argentina's Leonardo Mayer reached round two with a 7-6 (10/8) 6-3 triumph over German Mischa Zverev.
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