US Open finalists in 2021, neither Emma Raducanu nor Leylah Fernandez made it beyond the first round at the Madrid Open.
Raducanu, who is set to drop out of the WTA's top 100, withdrew from her first-round meeting with Viktoriya Tomova on Wednesday due to a hand injury.
The 20-year-old Briton has endured a difficult season, with her best performance coming at the Indian Wells Open, where she lost to world number one Iga Swiatek in the last 16.
Fellow youngster Fernandez has also struggled, and she came unstuck against world number 194 Mirra Andreeva, who progressed 6-3 6-4.
The big shock came as Jaqueline Cristian, ranked 525th in the singles rankings, defeated 2017 US Open champion Sloane Stephens.
Having taken the first set, Stephens looked set to book her place in round two, only for Romanian Cristian to prevail 5-7 6-4 6-4.
Alize Cornet overcame world number 39 Elena-Gabriela Ruse 6-7 (6-8) 6-4 6-3, while Camila Giorgi was forced to retire from her match with Mayar Sherif before the start of a deciding third set, and Amanda Anisimova was another top-50 casualty.
Rebeka Masarova, Nuria Parrizas Diaz, Marina Bassols Ribera and Irene Burillo Escorihuela carried the flag for Spain into the next round.
Eugenie Bouchard got the better of Dayana Yastremska as her return to top-level tennis continues.
Emma Raducanu promises more after reaching Stuttgart Open quarter-finals
Emma Raducanu says the best is yet to come as she continued her excellent form by making it through to the quarter-final of the Stuttgart Open.
The 2021 US Open champion beat Linda Noskova 6-0 7-5 in Germany to set up a mouth-watering last-eight tie with world number one Iga Swiatek on Friday.
Raducanu is making her way back after a torrid 2023 but looked excellent in winning her two ties in the Billie Jean King Cup at the weekend and then followed that up by swatting home favourite Angelique Kerber aside in Wednesday’s first round.
She stepped it up again to dispose of the world number 31 to set up a repeat of the 2022 quarter-final with Swiatek.
Despite all her troubles since winning the US Open in 2021, Raducanu never doubted the good times would return.
“I am not too surprised because I have been working really hard on the training court and I knew it was just a matter of time,” she said in her on-court interview.
“This isn’t my best I still have a long way to go. I am just really happy the rewards are starting to come on the match court.
“You know how it is when you are training day in, day out you feel like the results aren’t going your way. It is never that far away, that is something I am learning.
“Going through everything I have been through gives you a different appreciation, there is nothing like playing in front of fans and playing good tennis.”
Her progress will face its toughest test when against the Polish world number one, who is a master of the clay court, but the Briton knows she is not under any pressure.
Raducanu, whose world ranking of 303 will shoot up, added: “We played here two years ago in the quarters, I have come a long way in two years, and she has achieved a lot, I have nothing to lose, I can swing and enjoy it.
“Hopefully recover in time. I’m good.”
Emma Raducanu records impressive victory over Angelique Kerber in Stuttgart
Emma Raducanu claimed an emphatic 6-2 6-1 win over former two-time champion Angelique Kerber in the last 32 of the Porsche Grand Prix in Stuttgart.
Fresh from helping Great Britain reach the finals of the Billie Jean Cup at the weekend, Raducanu continued her promising form on clay by breezing past the home favourite.
Both Raducanu and Kerber were playing as wild cards in Stuttgart, with the Briton tumbling down the rankings after time out to undergo three surgeries.
Meanwhile former world number one Kerber only recently returned from 18 months out on maternity leave.
Raducanu got off to a flying start by breaking Kerber in the opening game and despite an immediate response from the German, the 2021 US Open champion took control and claimed the first set in 41 minutes.
Kerber was broken again at the start of the second set and although she managed to haul back level, Raducanu stepped up a gear and shrugged off a brief visit from the trainer to wrap up an emphatic win.
Also in Stuttgart, reigning US Open champion Coco Gauff rallied from 4-2 down in the deciding set to overcome fellow American and world number 134 Sachia Vickery 6-3 4-6 7-5.
And Tunisia’s Ons Jabeur finally snapped a five-game losing streak to beat Ekaterina Alexandrova 2-6 6-3 7-6 (1), telling reporters: “I thought about withdrawing so many times because I couldn’t take another loss.”
In Rouen, Naomi Osaka’s return to clay was cut short by a 6-4 6-2 first round defeat to Martina Trevisan.
Like Kerber, Osaka only recently returned to the tour following maternity leave, and was competing as a wild card.
In the Oeiras Ladies Open in Portugal, Britain’s fifth-seeded Harriet Dart suffered a 6-3 6-1 defeat to home player Matilde Jorge.
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