Jan Lennard Struff defeated Stéfanos Tsitsipás 6–4, 6–4 in the second round of the ATP 250 Halle event on grass on 20 June 2024, claiming a significant upset victory over the pre-match favourite. Despite Tsitsipás entering as the odds-on favourite at 1.91, the German produced a composed performance to secure a straight-sets win and advance to the quarter-finals. Struff's grass-court credentials proved decisive in the encounter, with the German maintaining control throughout both sets. The result marks a notable scalp for Struff and raises questions about Tsitsipás's form on the surface ahead of the grass-court season's climax.