[4] Dimitriades first attracted national attention for his co-starring role as Nick Polides in the 1993 Australian romantic comedy film The Heartbreak Kid, for which he received positive reviews and acclaim.

[5] In 1998, he played the protagonist Ari in the Ana Kokkinos film Head On, based on the book Loaded by Christos Tsiolkas.

[6] The film was controversial for its graphic violence, sex scenes and LGBT subject matter, but it earned mostly positive reviews.

[12] The following year, Dimitriades played estate agent Steve George in the television soap opera Neighbours.

[15] In 2015, he starred in The Principal, a SBS four-part crime drama screened over two weeks in October, for which he won a Logie Award.

In late 2018, Dimitriades had a recurring role in the BBC One drama The Cry as Detective Peter Alexiades and in the Netflix series Tidelands, again playing a police officer.

In 2021, Dimitriades appeared in the second season of ABC drama Total Control (TV series) in the role of Nice Pearce.

[18] In 2022, Dimitriades played the Greek gangster, Kosta, in the TV series The Tourist with Jamie Dornan and Danielle Macdonald.

[19] In 1996 and 1997, Dimitriades, along with Nick Giannopoulos and Vince Colosimo, toured as part of the Wogboys comedy stage shows.

[citation needed] Dimitriades, an avid collector of vinyl records, has stated that his love of music started in childhood.