Lorenzo Sonego defeated Brandon Nakashima 6–7, 7–6, 7–6, 3–6, 7–6 in a five-set encounter at Wimbledon's second round on grass on 5 July 2025. The result constituted an upset, with Nakashima entering as the pre-match favourite at 1.52 odds against Sonego's 2.74. The match proved extraordinarily tight across the opening three sets, each decided in tiebreaks before Nakashima claimed the fourth set to force a decider. Sonego ultimately prevailed in the fifth-set tiebreak, demonstrating resilience and composure on the grass court. The Italian's victory represents a significant scalp against a higher-seeded opponent and propels him into the third round, whilst Nakashima's exit marks a disappointing early departure from the tournament.