Phillips then moved on to the Canadian Football League. He had some difficulty getting a Canadian work visa due to his criminal record, but was eventually cleared to join the Montreal Alouettes. He showed signs of his old form, notching 1,022 yards, 13 touchdowns and a spot on the CFL Eastern All-Star Team while helping lead them to the 90th Grey Cup. However, he showed signs of lapsing into his old habits off the field. He walked out on the team at least once during the season, and his agent severed ties with him twice.