Benoit Paire rallied to upset second-seeded Tommy Robredo 2-6, 6-3, 7-5 and advance to the quarterfinals of the Hamburg Open on Wednesday.
Third-seeded Roberto Bautista Agut made an early exit as well, losing 7-6 (2), 7-6 (7) to Aljaz Bedene.
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Bedene will next play eight-seeded Fabio Fognini, who needed three sets to overcome Albert Ramos-Vinolas, 6-2, 3-6, 6-3.
In another upset, sixth-seeded and 2012 Hamburg winner Juan Monaco went out against qualifier Lucas Pouille, 6-1, 7-5. Pouille will next meet Paire.
Fifth-seeded Pablo Cuevas edged Diego Schwartzman 7-6 (4), 6-4 in a first-round match and Jiri Vesely completed a 3-6, 6-1, 6-0 win over Andreas Haider-Mauer in a match that had been halted by rain a day earlier.
Vesely will play top-seeded Rafael Nadal in the second round.