Top seed Tim Henman lost 6-4, 4-6, 6-2 to big-serving Croatian Ivan Ljubicic in the Madrid Masters third round on Thursday.
Ljubicic broke the struggling Briton's serve in the 10th game to claim the first set.
Henman began the second set with a tense, lacklustre game but revived after saving two break points when he was 3-2 down, going on to claim Ljubicic's next service game before levelling the match.
The third set started tightly but an increasingly frustrated Henman made a series of unforced errors to trail 5-2 before he handed Ljubicic victory with a wide forehand.
