However, after Pat Quinn replaced general manager Jack Gordon, Woodley was sent to Milwaukee to start the 1988–89 season in the IHL.
He was traded in a swap of first-round picks, to the Montreal Canadiens in exchange for Jose Charbonneau.
Woodley's lack of success (5 games played 2 goals) was surprising, given his high place in the 1986 draft.
In contrast, future Hockey Hall of Fame defender Brian Leetch, was selected 2 picks later than Woodley by the New York Rangers.
Dan Woodley has the distinction of being the only Oklahoma native ever selected in the first round of the NHL draft.