Emma Raducanu missed out on a second successive clay quarter-final as she was beaten at the Madrid Open by Anhelina Kalinina.
The British No. 1 fought back after dropping the opening set in the last-16 clash but lost 2-6 6-2 6-4 in two hours and 17 minutes.
Kalinina will next face Jil Teichmann after she beat world No. 16 Elena Rybakina 6-3 6-1.
World No. 37 Kalinina looked a tricky test for Raducanu, having taken a set off world No. 1 Iga Swiatek in Indian Wells and making the quarter-finals on clay in Charleston.
She played an impressive first set as she broke twice, including in the opening game, to pull ahead.
Raducanu seemed to be troubled by a back issue and took a medical time-out at the end of the set.
A double fault in Kalinina’s opening service game of the second set gave Raducanu, who made the quarter-finals in Stuttgart in her last tournament, an opening and she took it to grab some momentum.
The two players traded breaks before Raducanu closed out the set to take it to a decider.
Kalinina upped her level at the start of the third set and powered her way into a 3-1 lead. However, after squandering a chance to take further control at 15-40 on Raducanu’s serve, Kalinina played a poor service game and was broken.
Raducanu looked to be in the ascendancy as the unforced errors started to mount for Kalinina.
But the 19-year-old couldn’t take full advantage of the opportunity and Kalinina broke for 5-4 after a stunning winner.
A nervy finish saw Raducanu spurn a break point before Kalinina closed out a memorable win.
Sara Sorribes Tormo overcame Daria Kasatkina 6-4 1-6 6-3 in a match that featured 18 breaks of serve.
Sorribes Tormo is the last Spaniard standing in the draw after Paula Badosa and Garbine Muguruza both lost early.
She will next face 12th seed Jessica Pegula after she beat Bianca Andreescu 7-5 6-1.