The Shootout is a single elimination tournament held annually in autumn following the Club Championship. The field consists of 19 players who qualified for the tournament by shooting the lowest net rounds throughout the year. One player is eliminated on each hole and the last man standing on the 18th green is the Shootout Champion. The tournament begins on Saturday at noon with all nineteen players teeing off on the first hole. The player who nets the highest score is eliminated. Ties are settled by a chip off. Play continues until sundown with as many holes completed as possible and resumes the next day at sunup.
The following rule changes for the Shootout have been approved by the Winterwood Board:
- Handicap for each player will be the lower of either their qualifying handicap or current handicap at time of play
- One stroke handicap maximum on par 3s regardless of player's handicap
- Any ball in a hazard during a chip off is out of play regardless of proximity to the hole
- Any qualifying member who fails to renew his membership by the deadline will be removed from the list and will have to requalify upon renewal of his membership