Rafael Nadal suffered his second defeat in as many matches after going down 3-6 6-1 7-5 against Alex de Minaur at the United Cup.
The 22-time grand slam champion, who was also beaten by Great Britain's Cameron Norrie in his opening match, is still seeking his first victory of the season with the Australian Open just around the corner.
Home favourite De Minaur delighted the Sydney crowd by recovering from a set and break down to claim his maiden win over the world number two.
"I think it's definitely up there [as one of my best wins]," he said. "It's one of those achievements that you have unlocked in your career.
"But also, it's a big win for myself, one that I really needed. I'm going to cherish and use, take all the confidence from this and be able to hopefully take it to have a good [Australian] summer."
Spain and Australia are unable to progress to the City Finals, but Nuria Parrizas Diaz levelled the Group D tie with a 6-1 6-3 victory over Maddison Inglis.
The USA, who required just two points against Germany to advance to the next stage, set up a showdown with Great Britain after Taylor Fritz and Madison Keys enjoyed straight-set successes over Alexander Zverev and Jule Niemeier respectively.
Italy moved to the brink of joining them in the City Finals after taking a 2-0 lead over Norway. Lorenzo Musetti overcame Viktor Durasovic in straight sets, while Martina Trevisan edged out Malene Helgo in three.
Greece require one win from their final three matches against Belgium to also advance, Stefanos Tsitsipas hit 12 aces on the way to defeating David Goffin 6-3 6-2 to level the Group A showdown at 1-1.
Poland's winner-takes-all Group B clash with Switzerland is also finely poised at 1-1. World number one Iga Swiatek beat Belinda Bencic 6-3 7-6 (7-3), before Marc-Andrea Huesler's 6-3 6-2 victory against Daniel Michalski.
Andreescu tore ankle ligaments in Miami as US Open winner gives update on WTA Tour lay-off
Bianca Andreescu has revealed she tore ankle ligaments and faces time on the sidelines after her excruciating injury blow at the Miami Open.
Former US Open champion Andreescu, who in 2019 beat Serena Williams in what proved to be the American great's last grand slam final, is set to miss at least the start of the clay-court season.
The Canadian 22-year-old was enjoying an excellent run in the Miami event, knocking out Emma Raducanu, Maria Sakkari and Sofia Kenin en route to the last-16 stage.
She dropped the first set against Ekaterina Alexandrova on Monday but was an early break to the good in the second when injury struck, forcing her to abandon that fourth-round match.
Andreescu howled in pain on the court after suffering the ankle blow and needed to be taken away in a wheelchair.
She joked the day after: "Woke up with a brace on my foot… anyone know what happened?"
Now she knows exactly what happened, and the news is not particularly good.
Andreescu posted on Twitter: "Results show that I've torn 2 ligaments in my left ankle. It's tough to say exactly how long it will take, but let's just say it could've been much worse!!
"I'm going to take it day by day, and I am optimistic that with the right work, rehab, and preparation, I'll be back on court soon. Rehab process has already started and will continue to give updates."
Andreescu has suffered a string of injuries since becoming a teenage grand slam winner. She sits 31st in the WTA rankings, having been as high as number four in October 2019.
Miami marks the end of a hardcourt swing on the tour, with clay set to take over for two months, starting in Charleston at a WTA 500 event next week.
Sinner advances to maintain excellent Miami Open form, evening session cancelled due to rain
Italian 10th seed Jannik Sinner downed Emil Ruusuvuori to secure his berth in the Miami Open semi-finals along with bringing up his 20th win of the season on Wednesday.
Sinner, who dropped only one point on first serve, won 6-3 6-1 over the Finn in one hour and 16 minutes.
The 21-year-old Italian will face either top seed and defending champion Carlos Alcaraz or 2022 Indian Wells winner Taylor Fritz in the last four. Sinner lost to Alcaraz in the Indian Wells semi-finals a fortnight ago.
Alcaraz and Fritz's Miami quarter-final was postponed to Thursday with persistent rain forcing the evening session in Miami to be cancelled.
The other quarter-finals between 14th seed Karen Khachanov and 25th seed Francisco Cerundolo along with fourth seed Daniil Medvedev and qualifier Christophr Eubanks were also re-scheduled for Thursday.
The Sinner-Ruusuvuori clash was also impacted by a two-hour rain delay, but the Italian prevailed to maintain his perfect record in Miami, having not dropped a set.
"We both played well today but I won the important points," Sinner said. "It's never easy when you are up and you get interrupted, but I came back and played well."
Sinner's run to the Miami semi-finals has seen him drop the fewest games (23) since Rafael Nadal (21) and Novak Djokovic (23) in 2014.
The Italian became the seventh male to reach the semi-finals at both Indian Wells and Miami in a single year before turning 22, joining an elite list in Andre Agassi (1990), Jim Courier (1991), Djokovic (2007), Andy Murray (2007 and 2009), Nadal (2008) and Alcaraz (2022).
Sinner's 2023 record is now 20-4, bettered only by Medvedev (26-3) and Cameron Norrie (21-5).
Cirstea stuns second seed Sabalenka in straight sets in Miami Open quarters
World number 74 Sorana Cirstea produced a major shock in the Miami Open quarter-finals after toppling 2023 Australian Open champion Aryna Sabalenka in straight sets on Wednesday.
The 32-year-old Romanian triumphed 6-4 6-4 over the in-form Belarusian to progress to her first WTA-1000 semi-final for a decade, dating back to the 2013 Canadian Open in Toronto.
World number two Sabalenka came into the contest as the highest remaining seed after Iga Swiatek's withdrawal, having won a tour-leading 20 matches this season.
But Cirstea blew Sabalenka away in one hour and 27 minutes, maintaining her fine run in Miami where she has not dropped a set in five matches.
Sabalenka hit more winners than Cirstea (21-16) but the Romanian was more polished, committing only nine unforced errors compared to the Australian Open winner's 21.
Cirstea broke Sabalenka in the first game of each set and showed resolve when she served out victory from 15-40 down.
"I think I'm a bit speechless," Cirstea said after the match. "I came out knowing that it's going to be a really tough match. Aryna hits so hard, so I knew I had to hold my ground, and I'm very, very happy with my performance today."
Cirstea's list of scalps includes fifth seed Caroline Garcia, former top 20 player Karolina Muchova and now Sabalenka.
The Romanian also reached the quarter-finals at the Indian Wells Open a fortnight ago, losing to Swiatek in the last eight.
Cirstea will need to wait to learn her semi-final opponent with the quarter-final between 15th seed Petra Kvitova and 18th Ekaterina Alexandrova re-scheduled to Thursday after the evening session was cancelled due to persistent rain.
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