League matches run 20–22 December with first ball at 9:30 and matches at roughly 10:45, 12:00, 14:00 and 15:15. The semi-finals and final are on 23 December from 10:00. Teams must be ready 15 minutes before their start time; a team that fails to appear within 15 minutes may forfeit.

Expected match-day temperatures are 2–6°C and frost delays are possible before the first ball. Gloves and thermals are advised; hot drinks are served pitchside all day.

Five overs a side, one over per bowler, two points a win, net run rate splits ties, and the umpires’ word on weather is final. A match takes 45–60 minutes. Lightning stops play immediately; rain can shorten matches; frost, darkness or an unsafe ground can delay them. The tournament is run by the Winn Family Association’s Tournament Committee under the Winter Cup 2026 Handbook (in full on the Association website).

Winn At All Cost were crowned the first Winter Cup champions after an unbeaten run, beating Daddy Declan’s Dominators by 40 runs in the Grand Final on 23 December 2025. Evelyn Winn (70), Katie Winn (50) and Tyrone Winn (27 off 12) took Winn At All Cost to 191/6; Diane Winn’s 81 off 37 balls with six sixes lit up the reply before Evelyn Winn’s six wickets kept the Dominators to 151/6. Four individual centuries were scored in the tournament — Tyrone Winn 153 and 129, Alex Winn 128 and Katie Winn 125.