He spent two years working at Reserve, in Melbourne's Federation Square where, at the age of 24, he won Young Chef of the Year, Best New Restaurant and two chef's hats in The Age Good Food Guide. In 2004, the Global Food and Wine Magazine voted him as one of the Top 40 chefs of influence in the world. In 2006, Calombaris opened his own restaurant in Melbourne, The Press Club designed by renowned restaurant architects Mills Gorman. In 2008, he opened two other restaurants in Melbourne, Maha Bar and Grill (with chef Shane Delia) and Hellenic Republic (with chef Travis McAuley) both in collaboration with Mills Gorman. Also in 2008, he opened his first international restaurant, The Belvedere Club, in a hotel on the Greek island of Mykonos. In December 2010, Calombaris teamed up again with Mills Gorman to open P M 24 with culinary legend Philippe Mouchel. In 2011, he opened St Katherine's in Kew, again with Shane Delia and Mills Gorman. In January 2012 he opened Mama Baba located in South Yarra, Melbourne. In July 2019, The Press Club closed, and was replaced by a new restaurant, Elektra.