Coco Gauff suffered back-to-back defeats in her respective doubles matches as her hopes of an Olympic gold medal were dashed at Roland-Garros.
In her first game of the day, Gauff teamed up with world number six Jessica Pegula to face Czech Republic duo Karolina Muchova and Linda Noskova.
After taking the first set, Gauff and Pegula were unable to continue their momentum, falling to a 6-2 4-6 5-10 defeat.
The American pairing started strongly and raced into an early lead, taking the opening set in what seemingly looked like a straightforward victory for Team USA.
However, Muchova and Noskova rallied and in a second set that saw five break points converted by both, the Czech's would prevail to take the game to a decider.
Gauff and Pegula lost four straight games to put their opponents in the ascendency, with Muchova and Noskova able to see out the win to progress to the quarter-finals.
Gauff emerged back onto the clay courts in the French capital for her mixed-doubles match soon after, joining Taylor Fritz to face a Canadian pairing of Felix Auger-Aliassime and Gabriela Dabrowski.
The American duo would come from a set down to take the game to a decider, but it would be their opponents who emerge 6-7 (2-7) 6-3 8-10 victors.
Gauff and Fritz exchanged blows with the Canadians, but were edged out in a first set tie-break after losing four games on the spin.
But not wanting to let their dreams of a medal die, the American pair would recover from losing an early break point to rally and earn one of their own in the eighth game, seeing out the win to take Gauff to her second third-set decider of the day.
However, the same result would transpire, with Auger-Aliassime and Dabrowski edging a nail-biting conclusion to book their place in the quarter-finals of the competition.
Canada advance to Olympic quarter-finals despite points deduction
Canada advanced to the knockout stages of the Paris Olympics against all the odds following a 1-0 victory over Colombia in Marseille.
The defending Olympic champions had won both their group matches, but were docked six points after being found guilty of using a drone to spy on New Zealand's training session ahead of their opening match of the Games.
It subsequently saw head coach Bev Priestman banned from football-related activities for a year, and despite appealing the decision, saw it rejected.
However, Vanessa Gilles' header proved to be the difference as she rose highest to meet Jessie Fleming's corner kick delivery in the 61st minute.
While Canada only took three points from their group games, they joined both Spain and the United States as the only teams to win all their games at the tournament so far.
Colombia, who started the day's action in second, settled for third spot but advanced to the knockout stages as one of the best third-placed teams and will face Spain.
Canada, meanwhile, will continue their quest for a second Olympic triumph in the Parc des Princes on Saturday where they will face Germany.
In the other Group A fixture, hosts France confirmed their place in the knockout stages of the competition after a hard fought 2-1 triumph over New Zealand.
Marie-Antoinette Katoto scored the opening goal of the game in the 22nd minute, only for Kate Taylor to respond for the visitors two minutes before the interval.
Katoto, who scored a brace against Colombia in their opening group game, notched her second double of the tournament late on to take her tally to five at the Games and secure top spot for the French.
France will next be in action this Saturday in Nantes, where they will face Brazil, who will be without veteran striker Marta following her red card against Spain earlier in the day.
Hayes maintains unbeaten Olympics start as United States top Group B
Emma Hayes' unbeaten record as the United States head coach continued as her side remained perfect following their 2-1 win over Australia in Group B.
Hayes, who took charge of the USWNT in May, has won six of her seven games at the helm, conceding just twice in that time.
The USA, along with Spain, are the only two sides to win all of their games at the Paris Olympics so far and will have great confidence heading into the knockout stages.
Trinity Rodman's second goal of the tournament two minutes from half-time sent them on their way, as Korbin Albert's 77th-minute strike saw her become the the youngest substitute scorer for the USA at the Olympics since Mallory Swanson against Colombia in 2016.
Alanna Kennedy's late strike would take some of the shine off an otherwise impressive display, but the United States dominated from the first whistle.
Hayes' side accumulated an expected goals (xG) of 2.82 from the 21 shots they had compared to Australia's 0.46, ending the match with 71.7% possession.
The United States will face Japan in the quarter-finals of the tournament, while Australia face a nervous wait to see if they qualify as one of the best third-placed teams.
In the other Group B encounter, Germany confirmed their place in the knockout stages alongside the United States following a comfortable 4-1 win over Zambia.
Lea Schuller opened the scoring in the 10th minute, with Klara Buhl adding the Germans second of the afternoon shortly after the restart.
Zambia captain Barbra Banda threatened to make the encounter a more difficult affair with her fourth goal of the tournament two minutes later.
But Schuller and Elisa Senß would add further gloss to the performance soon after to secure second place in the group.
Germany's triumph sets up a meeting with the runners-up of Group A, which could be either one of Colombia, France, Canada or New Zealand.
Nadal and Alcaraz stunned by Krajicek and Ram at Paris Olympics
Austin Krajicek and Rajeev Ram stunned gold medal favourites Carlos Alcaraz and Rafael Nadal to reach the semi-finals of the Paris Olympics.
In what could be Nadal's final appearance at Roland-Garros, the American duo showed no mercy, prevailing in straight sets 6-2 6-4 to advance to the next round.
After beating Roman Safiullin to reach the quarter-finals of the singles earlier that day, Alcaraz started slowly as the Spanish pair found themselves immediately behind.
Nadal and Alcaraz would close the gap to 3-2, but their American opponents would continue their dominance, taking the next three games to see out the first set.
The Spaniards started much better in the second, with the pairs trading blows and each holding their own serve.
But the decisive break would come in the seventh game, with Krajicek and Ram going to within two games of producing an unlikely upset against the pre-tournament favourites.
The Spaniards then missed two break points to take the game to 5-5, with the Americans missing two match points of their own in a thrilling final set.
But it was Krajicek and Ram who would emerge victorious, dumping out Nadal in what may be his last dance on the court.
They will face Czech Republic duo Adam Pavlsek and Thomas Machac for a place in the final on Saturday.
Data Debrief: Nadalcaraz no match for American duo
The fairytale ending for Nadal has come to an end, but it took an impressive display from Krajicek and Ram to do so.
The Americans won 25 of their 57 return points compared to Nadal and Alcaraz's 19, and converted all three of their break points.
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