Returning to Canada, Roberts signed a three-year, $8 million contract with the Toronto Maple Leafs. He chose his hometown Maple Leafs because he felt they had a better opportunity to win the Stanley Cup than Carolina did. He recorded 53 points in 2000–01 and his 29 goals led the team. A 48-point season followed in 2001–02 and he assumed leadership of the Maple Leafs during the 2002 Stanley Cup Playoffs after team captain Mats Sundin suffered an injury. Roberts led Toronto past their first round opponent, the New York Islanders, in an occasionally violent seven game series. Roberts contributed to this violence in game five, with a hit that drove Kenny Jonsson into the boards head-first, leading to a season-ending concussion for Jonsson. Roberts was assessed a major penalty, but, surprisingly, was not suspended. The Maple Leafs reached the Eastern Conference final, where they ultimately lost to Carolina. Roberts led Toronto in playoff scoring with 19 points in 19 games.