[1] Dilena started his career at South Australian National Football League (SANFL) club Sturt and was involved in a controversial incident late in the 1988 SANFL season when he was knocked unconscious from a charge by Russell Johnston.
The Port Adelaide captain was suspended for five weeks and as a result missed playing in their premiership winning team.
[3] In 1992, his final season, Dilena played just twice, but put in another good effort against Adelaide when he kicked a career high four goals.
[3] Dilena joined the North Melbourne Football Club board in 2008, and he was CEO from 2013 to 2019.
[4] In October 2022, Dilena joined the St Kilda Football Club board as Chief Operating Officer.