Rafael Nadal is chasing a 12th French Open title while 2009 champion Roger Federer is playing in the tournament for the first time since 2015.
Eighth seed Kei Nishikori began to suffer early in the first set and was a shadow of his usual fighting self as he lost it in 31 minutes.
Novak Djokovic came through an almost three-and-a-half hour, four-set grind that extended into the early hours of Tuesday.
Novak Djokovic remained on course for a record seventh Australian Open title but will next have to conquer marathon man Kei Nishikori.
US Open champion and fourth seed Osaka swept past Slovenia's Tamara Zidansek 6-2, 6-4.
The Japanese had set his sights on returning to the world's top five after falling to 39 last April due to a wrist injury.
Daniil Medvedev beat Andy Murray in straight sets in the Brisbane International on Wednesday.
The 31-year-old Scot had intended to play in Brisbane at the beginning of 2018 but was forced to withdraw with a hip injury.
Roger Federer is now in danger of failing to qualify for the semi-finals for just the second time in 16 appearances at ATP Finals.
Roger Federer and Novak Djokovic, along with six fellow tennis stars travelled to Westminster by the London Underground.
Third seed Nishikori won the last of his 11 career titles in Memphis two years ago.
Novak Djokovic boasts a 14-4 lead over Juan Martin del Potro in a 10-year rivalry, including two wins without dropping a set at the US Open in 2007 and 2012.
Third seed Juan Martin del Potro, the champion in 2009, was 7-6 (7/3), 6-2 ahead when Rafael Nadal retired.
Two-time champion Novak Djokovic ended John Millman's fairytale US Open run on Wednesday, beating the 55th-ranked Australian in straight sets to book a semi-final clash with Kei Nishikori.
Kei Nishikori and Naomi Osaka made history at the US Open on Wednesday when they became the first Japanese man and woman to reach the semi-finals at the same Grand Slam.
Nishikori could find himself up against Marin Cilic for a place in the semi-finals.
Alexander Zverev will face 10th-seeded Greek 19-year-old Stefanos Tsitsipas in the ATP Washington Open semis.
Three-time champion Novak Djokovic reached his eighth Wimbledon semi-final on Wednesday with a 6-3, 3-6, 6-2, 6-2 win over Japan's Kei Nishikori in a stormy Centre Court clash.