It all began in 2001 with an original field of four teams representing Glenview CC, Hacienda Hills CC, Orange Blossom Hills CC and Tierra Del Sol CC. Hacienda Hills emerged the winner of the inaugural tournament defeating Glenview CC in the finals.
Glenview CC would take the next 3 Cups in an incredible three peat defeating Hacienda Hills CC in all three cups from 2002 - 2004. In 2005, The Cup would grow to six teams and Orange Blossom Hills CC would began a reign that ended with yet another three peat in the early history from 2005 - 2007 defeating Glenview CC, Tierra Del Sol CC and Lopez Legacy CC respectively.
The Cup grew to 12 teams in 2016 with the addition of Belle Glade CC. Belle Glade entered as the number 1 seed after the qualification rounds. 2016 proved to be a battle to the end when Tierra Del Sol CC won 4 of the 6 foursome matches in the second round of the Championships against Bonifay CC to place themselves in contention for the final day of play. Both of these teams had suffered emotional losses when teammate Kathy Hooper (Bonifay) passed away one day before returning to The Villages and teammate Jean Holbert (TDS) collapsed on the course during the first day of Championship Week, and despite treatment did not survive an apparent aneurysm.
In the end, Team Bonifay who had never won a match in The Cup, walked away with their first Championship defeating Tierra Del Sol 13-11.
The 2017 Village Cup Championship came down to 8th seeded Belle Glade CC and 3rd seeded Evans Prairie CC. After the initial four ball round on Monday, Evans Prairie had the lead 3.5 to 2.5 over Belle Glade. After alternate shot play on Tuesday, Evans Prairie CC took 4 of the 6 matches and increased their lead going into the final day 7.5 to 4.5. That lead proved to hard to overcome and Evans Prairie won the championship 14.5 - 9.5 after singles play on the final day.
The 2018 qualifying rounds placed Havana CC as the number 1 seed ahead of the defending champions from Evans Prairie CC by one stroke. Battling through the qualifying rounds the stage was set for a Championship Week that would see Tierra Del Sol CC take on Belle Glade CC. Day one proved to be a challenge with Mother Nature throwing a one hour delay into the mix. The day ended with Belle Glade taking the lead 3.5 - 2.5 over Tierra Del Sol CC.
2001 Hacienda Hill CC
2002 Glenview CC
2003 Glenview CC
2004 Glenview CC
2005 Orange Blossom Hills CC
2006 Orange Blossom Hills CC
2007 Orange Blossom Hills CC
2008 Tierra del Sol CC
2009 Tierra del Sol CC
2010 Mallory Hill CC
2011 Mallory Hill CC
2012 Orange Blossom CC
2013 Palmer Legends CC
2014. Cane Garden CC
2015 Glenview CC
2016 Bonifay CC
2017 Evans Prairie CC
2018 Tierra Del Sol CC
2019 Bonifay CC
2020 Covid
2021 Bonifay CC
2022 Havana CC
2023 Bonifay CC
2024 Mallory Hill CC
2025 Southern Oaks CC
More info coming soon
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