Derek Armstrong (born June 19, 1981 in Perth, Ontario) is a Canadian football guard for the Winnipeg Blue Bombers of the Canadian Football League. He was drafted in the fifth round with the 38th overall pick in the 2006 CFL Draft by the Calgary Stampeders. He played CIS Football with St. Francis Xavier University. During the 2009 CFL season the Calgary Stampeders traded defensive lineman Odell Willis and receivers Titus Ryan, and Jabari Arthur to the Winnipeg Blue Bombers in exchange for receivers Romby Bryant and Arjei Franklin. These two teams also agreed that Armstrong would be involved in the trade, but would remain Calgary property until the end of the season, so following the 2009 season Armstrong was traded to Winnipeg.