Stockwood's first album, 1995's Bonavista, was a slow seller until it was rereleased in 1996 with an extra track. That song, "Jerk", became Stockwood's breakthrough hit both in Canada and internationally. Her other early singles included "She's Not In Love", "You Won't Remember This" and "Enough Love".
In 1999, Stockwood released her second album, 12 Years Old. The title track from that album was a moderate hit. She also released "You and Me" and a new radio remix for "Still" was the album's third single.
In 2002, Stockwood collaborated with close friends Tara MacLean and Damhnait Doyle to form the group Shaye, named after Tara Maclean's sister Shaye Martirano, who died as the result of injuries suffered in a motor vehicle accident. Shaye's debut album The Bridge was released in 2003 and "Happy Baby" the lead single, was nominated for Single of the Year at the 2004 Juno Awards. This was followed by "Beauty" in January 2005.
Their 2006 followup, Lake of Fire was released available on iTunes in November 2006, then released physically in February 2007.
In 2006, Stockwood released a Christmas CD called I Love Santa.
In March 2011, Stockwood released her fourth studio album Back to the Water. It includes performances with fellow Shaye band member Damhnait Doyle, and Newfoundland bands The Once and The Dardanelles.