Winstead finished 4-1 on the week as he competed against three conference opponents. He went 3-0 in singles play with wins at No. 3 against Henrique Castro of Emmanuel 6-1, 6-3 and No. 2 singles against Young Harris' Rodrigo Mendoza, 6-3, 7-5 and Lees-McRae's Andrew Kunaka 7-5, 6-1.
He split two doubles matches on the week as well in the No. 2 spot, earning a 6-0 win with Nicholas Caryover Andrew Kunaka and Andy Tallafigo of Lees-McRae.