Kiniski began wrestling in his native Canada for the first time in November 1956, debuting for Toronto's Maple Leaf Wrestling. His first main-event match in the territory took place at Maple Leaf Gardens in January 1957, when he teamed with Buddy Rogers against Whipper Billy Watson and Pat O'Connor and saw the beginning of a lengthy feud with Watson that spanned across Canada; the Kiniski-Watson feud gained national exposure due to their matches sometimes being seen on CBC Television. He also challenged NWA World Heavyweight titleholders Watson, Thesz and Dick Hutton for the title on several occasions between 1955 and 1957.