Baritone Bailey Montgomerie is an alumnus of Newtown High School of the Performing Arts in Sydney with several years of classical training. Bailey is currently studying Classical Voice and Politics and International Relations at the University of Melbourne and Melbourne Conservatorium.

Throughout his training, he has appeared in several Eisteddfods and recitals in Australia and abroad and has been invited to participate in masterclasses with singers such as Deborah Cheetham, Charlotte de Rothschild and Emma Matthews. Bailey has also been an auditioned member of ensembles such as Sydney Philharmonia Choir and Gondwana National Choirs and is currently a choral scholar with St Patrick's Cathedral Choir, and a member of Exaudi, and the Hamer Singers locally in Melbourne.