He averaged 34.7 points per game as a senior and led Austin to the 2002 2A Final Four and Mid-Southern Conference Championship.

[2] He averaged 18.2 points and 7.2 rebounds per game as a junior, despite playing out of position at power forward due to injuries.

[5] Winchester was selected by the Dodge City Legend with the fourth pick of the 2006 USBL draft.

[1] Winchester became an assistant coach at Bowling Green High School for the 2007–2008 season.

In July 2010, Winchester was hired as the head coach of Scottsburg Senior High School.

[8] Winchester was inducted into Western Kentucky's Athletic Hall of Fame in October 2019.