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Andy Murray's injury comeback was sidetracked as the three-time Grand Slam champion lost 6-1, 1-6, 6-4 to Lucas Pouille.
Novak Djokovic and Venus Williams also were among the Grand Slam champions who missed out on a first-round bye at the last major tuneup event for the US Open, which starts August 27 in New York.
The former world number one is now ranked 375 as he continues his comeback from an 11-month injury layoff.
Three-time Grand Slam champ Andy Murray played only two June grasscourt events in his comeback prior to coming to Washington.
Both stars are making comebacks from injuries. Britain's Murray missed 11 months with a right hip injury before reurning in June. Wawrinka was out eight months with a left knee injury.
Murray, ousted fourth seed Kyle Edmund 7-6 (7/4), 1-6, 6-4 in an all-British matchup to reach the third round of the hardcourt tuneup for the US Open.
Murray's career tally of 45 ATP World Tour singles titles includes a pair of victories at Wimbledon and one at the US Open.
Andy Murray has not played in a hardcourt event since Indian Wells last year when he lost his first match to Vasek Pospisil.
The two-time champion made his debut as a BBC commentator for the quarterfinal between Rafael Nadal and Juan Martin del Potro.
Raonic, who was runner-up to Andy Murray in 2016, will face American Mackenzie McDonald in the last 16 on Monday.