Dominic Stricker defeated home favourite Lorenzo Musetti in five tie-break sets to make it two wins from two at the ATP Next Gen Finals and advance to the semi-finals.
The world number 111, who is seeded sixth in Milan following a flurry of withdrawals, defeated Musetti 4-3 (7-5) 4-3 (8-6) 3-4 (9-7) 3-4 (8-6) 4-3 (7-3) in Wednesday's epic match that last two hours and 31 minutes.
Having become the first player in the tournament's history to win three successive tie-breaks in Tuesday's win against Jack Draper, Stricker advances with a match to spare.
Musetti now faces a winner-takes-all showdown with Jack Draper on Thursday after the latter recovered to defeat Tseng Chun-hsin 1-4 4-2 4-3 (7-2) 4-2.
In the Green Group, Francesco Passaro saved three match points to overcome Italian compatriot Matteo Arnaldi 4-3 (9-7) 2-4 3-4 (7-4) 4-3 (7-4) 4-3 (10-8).
In what will go down as one of the all-time great matches in Next Gen history, Passaro triumphed after two hours and 38 minutes to get off the mark with his first victory.
"I am very tired," he said. "It was a really long match and this format I think it is tough and physical.
"For me it was physical today, with the tension as well, I was cramping. It was not easy. I am really happy to win and I will enjoy."
Brandon Nakashima moved to the top of the standings with a 4-1 4-3 (7-2) 4-2 victory against Jiri Lehecka as the third seed made it back-to-back wins at the Allianz Cloud.
Emma Raducanu’s run at Stuttgart Open ended by world number one Iga Swiatek
Emma Raducanu’s progress in the Stuttgart Open was halted in straight sets by world number one Iga Swiatek.
The Polish four-time grand slam champion, in her 100th week on top of the ATP world rankings, prevailed 7-6 (2) 6-3 to set up a semi-final showdown with Kazakhstan’s Elena Rybakina.
It was, however, an encouraging quarter-final performance from Raducanu, who has slipped to 303 in the world rankings after a torrid 2023.
Raducanu came in to the contest on a high after winning four matches in a row for the first time since her US Open title in 2021 and raised confidence levels were reflected in the opening exchanges.
Several booming returns from the 21-year-old Briton turned a 0-40 deficit into an immediate break of serve, but Swiatek levelled after edging a second game that featured seven deuces.
That see-saw battle set the tone for a marathon 70-minute opening set which produced plenty of high-quality ground strokes from both sides of the net.
The match went with serve from that point, with Raducanu superbly holding her nerve at 5-4 and 6-5 down to force the first set to a tie-break.
Swiatek completely dominated the tie-break though, winning the first four points before closing it out 7-2.
Raducanu was quickly in trouble again in the second set, falling 2-0 behind and covered in clay after losing her footing on the baseline.
She continued to fight and fended off break points in her next two service games to stay in the match.
But Swiatek kept up the pressure to finally end Raducanu’s resistance to move in to the last four.
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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