In 2014, Winterbotham coached his first NCAA champions. Mikelis Libietis and Hunter Reese won the 2014 NCAA doubles title, beating Ohio State's Peter Kobelt and Kevin Metka 7-6 (4), 6-7 (3), 7-6 (6) in the final. Prior to this breakthrough, Winterbotham had coached four NCAA individual finalists: 2008 NCAA Singles – John-Patrick Smith; 2009 and 2010 NCAA Doubles – Smith and Davey Sandgren; and 2011 NCAA Singles – Rhyne Williams.
