Bowskill began performing at a young age, and first played on stage at the age of eleven at Jeff Healey's club in Toronto, Ontario. “They wouldn’t let an 11-year-old inside his club, so I started busking on the side- walk outside,” Jimmy recalls in Guitar Player Magazine “Jeff heard about me, invited me in to play, and I did pretty well. I got a lot of gigs and exposure just from that one night.” Healey's bassist, Alec Fraser, provided studio time for Bowskill, and eventually he signed a deal with Ruf Records. The next year he recorded his first album, Old Soul, and performed on the main stage at the Peterborough Folk Festival.

Bowskill's second album, Soap Bars and Dog Ears, was nominated for a Juno Award when he was fourteen years of age.

In 2005 he was presented with a Maple Blues Award as "Best New Artist of the Year".

In 2010, he toured in Europe with Joe Bonamassa and Jeff Beck. He also performed more locally at the Belleville Blues Festival.

In 2011, he released his first live album, Jimmy Bowskill Band Live, produced by Ruf Records.

In 2012, Bowskill introduced his album Back Number at the Kincardine Lighthouse Blues Festival. The album was recorded at Metalworks Studios in Mississauga, Ontario. He also performed at the Windsor International BluesFest and at the All-Canadian Jazz Festival in Port Hope with the Ganaraska Sheiks.

While on tour in 2009, the Jimmy Bowskill Band included Wayne Deadder on bass and Dan Neill on drums. In 2012, the band members were Ian McKeown on bass and Dan Reiff on drums.

In November 2015, Bowskill joined the Canadian rock band The Sheepdogs playing lead, rhythm and pedal steel guitar.

In 2016, Blue Rodeo released their album 1000 Arms, which includes Bowskill playing on two tracks.