A native of Westboro, Missouri, Wayne Winstead began his coaching career at Sheridan High School. His teams at Sheridan won more than 700 games and took 13 conference championships. He moved to Worth County High School in 1976, where his three year girls basketball record was 56-21. The three winning seasons he produced at Worth County were the first in the school's basketball history.
In 1979, Winstead moved to Maryville where he took over as coach for the Northwest Missouri State University Women's program. Winstead has taken the Northwest Missouri State teams to post-season play in thirteen of fourteen seasons. He earned MIAA Coach of the Year honors in 1984, after his 25-5 team won the conference and was ranked number one in the nation and eventually finished eighth in the nation as they upset national powers Southeast Missouri State University and Central Missouri State University.
Winstead continues to mount up wins at Northwest Missouri State, where he is the winningest baskeball coach in the University's history.