On March 25, 2007, Jackson was signed to a 10-day contract by the Toronto Raptors to provide bench depth. After performing well in limited minutes, he was signed to a second ten-day contract and then to a two-year pact with Toronto for the rest of the 2006–2007 NBA season, and the 2007–08 season as well. On April 18, 2007, in Toronto's last game of the regular season, Jackson exploded for a career-high 30 points and 5 assists while logging a career maximum 39 minutes in a defeat to the Philadelphia 76ers.