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Most recently, Bailey was the associate director and assistant fight director for As You Like It presented by Shakespeare BASH'd (directed by Drew O'Hara) which garnered rave reviews and a sold out run. Bailey is the former Editor-in-Chief of Intermission Magazine, an online magazine dedicated to engaging theatre audiences. She was the fight director for What I call her by Ellie Moon at Crow's Theatre. Last fall she participated in Tanisha Taitt's scene study class Come PLAY with Me. 

In March 2018, she played Lavinia in Hart House's production of Titus Andronicus directed by James Wallis (co-artistic director of Shakespeare BASH'd). In 2017, she played Eubulus in a staged reading of Gorboduc, (Shakespeare BASH'd) and Margaret in Much Ado about Nothing (Secret Shakespeare series). In the 2016 Toronto Fringe, she played Luciana and the Courtesan in The Comedy of Errors (Shakespeare BASH'd). The sold-out run received a NNNN rating from NOW Magazine.

Other theatre credits include: Arthur/Prince Henry in King John, Earl of Kent in Marlowe's Edward II (Shakespeare BASH'd), Ensemble in Oklahoma! (First Act Productions), Miss Prism in The Importance of Being Earnest (Hart House Theatre), Lady Smatter in The Witlings, Philostrate/Mustardseed in A Midsummer Night's Dream (Theatre Erindale), Second Woman in The Tin Can People (Edinburgh Fringe, Montreal Fringe).

Media credits include: Marcy (Lead) in I Love You More Than Vodka a Ryerson Media Arts film and Zoe (Lead) in Through Rose-Colored Glasses (Canted Pictures). Through Rose-Colored Glasses was recently accepted into the National Screen Institute of Canada. Bailey also played Julia in Killing Time with Canted Pictures which was an official 2015 selection for the Cannes Short Film Corner, Miami Independent Film Festival, the Chicago Int'l Arthouse Film Festival and more.
That’s a good thing for a body of work that has precious few strong roles for women by today’s standards, and O’Hara and associate director Bailey Green have incorporated these changes with a perceived minimum of changes to the original text, 'to synthesize the traditional with the modern'," - As You Like It review by Steve Fisher, My Entertainment World
Pure joy. - As You Like It review by Lynn Slotkin, The Slotkin Letter