Milos Raonic defeated Dennis Novak 6–7, 6–4, 7–6, 6–1 in the first round of Wimbledon on grass on 5 July 2023, in an upset victory against the pre-match favourite. Despite Novak holding marginally shorter odds at 1.91 to Raonic's 2.0, the Canadian recovered from losing the opening set via tiebreak to dominate the closing stages, securing the second set convincingly before edging another tiebreak in the third. Raonic's clinical performance in the fourth set, where he conceded just one game, underlined his growing control as the match progressed. The result represents a significant statement from Raonic on grass, his most successful surface, as he advances through the opening round of the year's third Grand Slam.