The First Annual South Bend Cubs Foundation Cubbie Cup Golf Outing was held on Monday, June 12, 2023, at Bent Oak Golf Club in Elkhart, Indiana. The inaugural event saw 18 teams vying for the traveling trophy and four tickets to the Boston Red Sox at Chicago Cubs game at Wrigley Field, donated by Cubs' Pitching Coach, Tommy Hottovy. Second place featured a South Bend Cubs' group ticket and merchandise package, with rounds of golf given for the longest drive, longest putt, and closest to the pin competitions.

Golfers and guests enjoyed a buffet lunch after the round, during which awards were handed out and raffle winners drawn. Prizes included Chicago Cubs and Iowa Cubs tickets, a Yeti cooler, autographed books from author, speaker, and former performance coach, Alan Stein Jr., a Cubs cooler basket, South Bend Cubs kids basket, and more.

For 2024, the Second Annual Cubbie Cup moves to Blackthorn Golf Club in South Bend. The event will feature a four-person scramble with a shotgun start, followed by lunch and awards. New this year will be a silent auction with the ability to bid online for those unable to attend in person.