Redmond led Norwich from the top of the lineup during a 2-0 week to open the 2026 season, remaining undefeated in both singles and doubles competition. Competing at No. 1 singles, he delivered a flawless performance in a season-opening 7-0 sweep over Vermont State University Lyndon, securing a dominant 6-0, 6-0 victory without dropping a game. Redmond followed with another strong showing against cross-divisional opponent Houghton University, battling through a competitive matchup at the top flight to earn a straight-set win, 6-4, 7-5, helping Norwich secure a 6-1 team victory. He also contributed significantly in doubles action, teaming with Terrance Bayly-Henshaw for victories at No. 1 doubles in both contests.  The pairing opened the week with a decisive 6-0 win before adding a 6-2 triumph against Houghton to help Norwich claim the doubles point.