Having a keen interest in Canadian television and how a comedy show was produced, Dimakos was soon hired as a Production Assistant on Buzz by MTR Entertainment.

During this time, Dimakos was attending improv classes at The Second City in Toronto and began writing stand-up material.

She partook in a week long stand-up comedy workshop at Humber College in 2003 under the guidance of veteran comedians Larry Horowitz and Mike MacDonald.

She was a series regular for network's hit show, Video on Trial, featuring on over 20 episodes along with the likes of Canadian comedians Russell Peters, Debra DiGiovanni and Trevor Boris.

Dini appeared on several episodes respectively as Posy Perennial, Matthew the Emo Girl, Dr. Pat McGroin, Belinda Belissima, Chandelier W. Bush (girlfriend of Boomer Phillips' character Lance Sherbourne), Rhonda the Housewife and most popularly as the daring nun, Sister Siobhan O'Shepardspie.

In February 2007, Dini was chosen as the opening act for veteran comedian Angelo Tsarouchas on the It's All Greek To Me Tour in Melbourne and Sydney, Australia.

That same year, Dimakos performed on the annual Accent on Toronto (6) - The Laughs Are On Us alongside Jean Paul and Frank Spadone.

As of March 2022[update], Dimakos' personal LinkedIn page shows that, following a career in entertainment from 1998 (as a fill-in radio host) to 2019, followed by schooling and training from 2019 to 2021, she is now Dini Dimakos Shevchenko, and is a Registered Social Service Worker (RSSW) with the Hills of Headwaters Collaborative Ontario Health Team, specifically part of the team located in Caledon, Ontario, providing support and caregiving to healthcare workers and their families throughout Dufferin County.

An article by Michele Henry focused on Dini's life as a Toronto comedian including where she performs, shops and resides in the city.