Maria Sharapova suffered a first defeat since returning from a 15-month doping ban as Kristina Mladenovic beat her in the semi-finals of the Stuttgart Open.
Five-time Grand Slam winner Sharapova, 30, was up a set and a break but squandered it to lose 3-6 7-5 6-4.
Mladenovic, 23, faces German Laura Siegemund in Sunday’s final.
Having been given a wildcard entry, Russian Sharapova needed to reach the final in Germany to be eligible for qualifying for the French Open.
Her defeat means she will be outside the top 200 when the rankings are released on Monday, so she will need a wildcard to compete in qualifying or the main draw in the event in Paris, which starts on 28 May.
She will learn on 16 May whether she will be given a wildcard for either stage at Roland Garros.