The eateries in question include Melbourne CBD venue Gazi, souvlaki chain Jimmy Grants, Yo-Chi frozen yoghurt stores and Calombaris' fine dining establishment, Press Club, to name a few.
The pending voluntary administration comes less than a year after the former MasterChef judge was forced to fork out $7.83 million in wages to 515 current and former employees.
Calombaris told the ABC at the time that he was "gutted" and "took full responsibility".
"We aren't closing our restaurants, we're here. And it's my job as their leader to keep pushing forward and keep speaking this message, not shying away from the mistake we made, but also acknowledging that we fixed it," he told the 7.30 program at the time.
"I won't forget that afternoon in 2017 when we sat there with my new business partners after we'd done a full audit for the business and discovered the underpayments."