NHL teams took interest in Oates following his junior season; at least five teams attempted to sign him. Choosing to forgo his final year of college eligibility, Oates signed a four-year, $1.1 million contract with the Detroit Red Wings that made him the highest paid rookie in the NHL in 1985–86. He made his NHL debut on October 10, 1985, against the Minnesota North Stars, scoring his first goal that night on goaltender Don Beaupre and added an assist. After this, Oates struggled offensively and was pointless in his following 16 games; the team subsequently demoted him to the Adirondack Red Wings of the American Hockey League (AHL). Oates split the remainder of the season between Detroit and Adirondack, finishing his first NHL season with 38 games played, 9 goals and 11 assists. In the AHL, he scored 18 goals and 28 assists in 34 games. Having finished the NHL season in Detroit, he was returned to Adirondack for the AHL playoffs which the team won to take the Calder Cup championship.