[10][11] During this time, he appeared in several made-for-television films, including Thicker Than Blood: The Larry McLinden Story, The Silence of Adultery, and Rose Hill, and as Noah Thompson in the "Let's Get Invisible!"

[12] His career received a major boost when he won the role of Josh Framm in Air Bud (1997), a film about a lonely boy who befriends a basketball-playing dog.

He also appeared in the short-lived American television series Titans (2000), opposite Yasmine Bleeth, for which he was chosen by producer Aaron Spelling.

Zegers had previously worked with Bleeth in the 1999 film It Came from the Sky, where he played a mentally disabled child visited by an angel-like couple.

[19] In the summer of 2003, he filmed the drama Some Things That Stay at the same time as the remake of Dawn of the Dead, shuttling across Canada between sets.

Zegers' performance as Toby Osbourne, the street-hustling bisexual son of a trans woman (Huffman) was praised by several critics, and he won the Trophée Chopard for Male Revelation at the 2006 Cannes Film Festival.

[21] Variety's reviewer wrote that "Zegers... finds multiple dimensions in pic's potentially most clichéd character...,"[22] and The Hollywood Reporter's critic said, "As a boy who considers sex his chief talent, Zegers... conveys Toby's essential sweetness and hunger for real affection, making him much more than just a vain or damaged kid.

He appeared in Rock Mafia's 2010 music video "The Big Bang", and in 2012, played the male protagonist in the television series Titanic: Blood and Steel.