Boris Becker has been accused of failing to hand over trophies - including the 1985 Wimbledon men's cup that catapulted him to sporting stardom - so they could be sold to settle his debts.
The 52-year-old German, who was declared bankrupt in June 2017, is accused of not complying with obligations to disclose information.
Trophies listed on a new 28-count indictment include his maiden Wimbledon trophy, his 1989 silverware from the same tournament, and his Australian Open trophies in 1991 and 1996.
He pleaded not guilty to all counts when he appeared in a London court on Thursday for a 45-minute hearing.
Becker, wearing a dark-grey suit, blue tie and a black face mask, spoke to confirm his name, to enter his pleas, and that he understood a warrant would be issued for his arrest if he absconded on bail.
He was told his trial would be listed to take place in September 2021.
Earlier, Becker, who has worked in TV since he retired, appeared to take a selfie as he entered the court building, in front of scores of assembled international journalists and photographers.
Prosecutor Rebecca Chalkley said Becker, who lives in London, may face further charges at a later date.
Defence counsel Jonathan Caplan said: "He (Becker) is determined to face and contest these charges and restore his reputation in relation to the allegations made against him."
Becker was arraigned on a series of charges that took more than 15 minutes to read to the court. They included concealing more than 1 million ($1.3 million) held in bank accounts, as well as property.
Becker is also accused of removing hundreds of thousands of pounds by transferring it to other accounts, including to former wife Barbara Becker, and estranged wife Sharlely "Lilly" Becker.
It is also alleged he hid his holding of shares in a firm called Breaking Data Corp.
Becker was released on bail ahead of his trial, which is due to last up to four weeks.
The German took the tennis world by storm as a 17-year-old as he became the then youngest-ever men's Grand Slam champion at Wimbledon in 1985, defending his trophy the following year.
Nicknamed "Boom Boom", he went on to win a further four majors and 49 singles titles in all, amassing $25 million in prize money.
Becker also enjoyed a successful spell from 2014 until 2016 as coach of Serbia's world number one Novak Djokovic.