 From 1995–98, Wingfield collected a further 94 regular season appearances, for the Portland Trail Blazers.On March 10, 1996, against the Indiana Pacers, he scored a career-high 17 points, adding seven rebounds and five assists (career-high tie) in a 113–108 win.His best month as a pro came in January of 1997 (his third season) when he scored in double digits five times, including a 14-point 12-rebound 2-assist 2-block game at Boston on January 31.