Cannon was traded to the Oakland Raiders before the 1964 season. Raiders head coach Al Davis liked Cannon's abilities but did not know how he wanted to use him. At first Davis moved Cannon to fullback, where he was an asset in catching passes, an attribute not all fullbacks then possessed. After a slow start, he finished the season with 37 receptions for 454 yards and eight touchdowns. He also rushed for three more touchdowns. Next season Davis moved him to tight end, to the chagrin of Cannon; he expected to be made into a wide receiver, but the Raiders had both Art Powell and rookie Fred Biletnikoff to cover that position. He eventually accepted his new role and adapted quickly to it. However, the tight end was seldom used in the Raiders' offense. He caught only seven passes that season with no touchdowns. Before the 1966 season, John Rauch took over as head coach as Al Davis became AFL commissioner and the Raiders' general manager. Cannon established himself as a deep threat in Rauch's offense and caught fourteen passes for 436 yards—an average of 31.4 yards per reception.