Emma Raducanu squandered set point in a second-set tie-break as she lost 0-6 6-7 (6) to Anhelina Kalinina in the opening round of the Qatar Open.
Raducanu had been granted a wild card for the first WTA 1000 event of the season in Doha, but slipped to a fourth defeat in seven matches since returning from injury.
The British number seven rallied bravely in the second set against Ukrainian Kalinina after a one-sided first set, which lasted little over half an hour.
Raducanu saved two match points at 6-5 down in the second set to force a tie-break and was one point away from squaring the match while leading that 6-5.
But world number 30 Kalinina held her nerve and will now face Latvia’s eighth seed Jelena Ostapenko in the second round.
Kalinina won the opening game of the match on Raducanu’s serve and broke the Brit twice more, while comfortably holding her own serve without facing any break points to take the opening set 6-0.
Raducanu came under immediate pressure at the start of the second set, losing her serve for the fourth consecutive time before responding to break back and win her first game of the match.
The following eight games all went with serve, with Raducanu saving five break points to lead 4-3.
After being broken for a fifth time in the match to trail 6-5, the Briton responded again, saving two match points against Kalinina’s serve to force a tie-break.
Raducanu served for the set at 6-5 up in the tie-break, but lost the next two points on her serve and Kalinina sealed victory on her third match point.
Keys downs Gauff to reach Madrid Open quarter-finals
Madison Keys is through to the quarter-final of the Madrid Open for the first time in her career after rallying to a 7-6 (7-4), 4-6, 6-4 win over Coco Gauff on Monday.
The 29-year-old trailed 5-2 in the first set and 4-2 in the third set but rallied in both to come from behind to beat the number three seed.
Despite winning the second set, Gauff struggled to find her rhythm, suffering from 13 double faults, including two in the final game.
Keys will face former Madrid Open champion Ons Jabeur for a spot in the semi-final after the number eight seed overcame Jelena Ostapenko in straight sets.
Data debrief: Keys reaches new milestone
Having lost in the first round in seven of her nine previous trips to the Spanish capital, Keys has now bettered her previous best finish in Madrid - a third-round showing in 2016.
Keys hadn't won three matches in a row since reaching the US Open semifinals last year.
Keys downs Gauff to reach Madrid quarter-finals
Madison Keys is through to the quarter-final of the Madrid Open for the first time in her career after rallying to a 7-6 (7-4), 4-6, 6-4 win over Coco Gauff on Monday.
The 29-year-old trailed 5-2 in the first set and 4-2 in the third set but rallied in both to come from behind to beat the number three seed.
Despite winning the second set, Gauff struggled to find her rhythm, suffering from 13 double faults, including two in the final game.
Keys will face former Madrid Open champion Ons Jabeur for a spot in the semi-final after the number eight seed overcame Jelena Ostapenko in straight sets.
Data debrief: Keys reaches new milestone
Having lost in the first round in seven of her nine previous trips to the Spanish capital, Keys has now bettered her previous best finish in Madrid - a third-round showing in 2016.
Keys hadn't won three matches in a row since reaching the US Open semifinals last year.
Nadal goes the distance to reach Madrid Open last 16
Rafael Nadal battled to victory over three hours on the court against Pedro Cachin at the Madrid Open on Monday to seal a 6-1 6-7 (5-7) 6-3 win to reach the last 16.
The former world number one looked back to his best as he cruised through the opening set but was pushed hard in the second by Cachin.
Nadal came from behind to level at 5-5, but Cachin eventually sealed the set on his third set point.
The Spaniard then rallied in the third set, cutting down on his errors to regain control and advance to the fourth round at a tour-level event for the first time since 2022.
Nadal is one step away from booking his place in a 10th consecutive quarter-final in Madrid and will face Jiri Lehecka on Tuesday in the next round after the 30th seed overcame Brazilian qualifier Thiago Monteiro in two sets.
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