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In the fall of 1994,  a few Villagers spotted a sign on CR 466 announcing "Polo Today...all welcome".  Turning down the Lane to The Oxford Polo Club, they were warmly welcomed by the Lyall family.  After thoroughly enjoying their experience, those Villagers invited other Villagers.  Anticipating 25 people, they were delighted when 75 residents showed up.  They formed The Villages Polo Booster Social  Club on October 22,1994.  Their objective was to tailgate with other members at future matches and promote the sport of polo. 

​In 1995, Gary Morse was introduced to polo by some local friends, the Moran's, Lyall's and Jim Parr who invited him to a polo match in Barbados.  He became so captivated by the sport, (he decided it would be a perfect activity for Villagers), that he invited "The Barbados Bajans" to play at The Villages.  Without a  polo field or polo team, he decided to hire Lord Lyall to coordinate all necessary components to create The Villages Polo Club as quickly as possible.   The Booster club continued to attend matches at The Oxford Polo Club.

In the spring of 1997, the Bajans played their first game at The Villages Polo Club, to the delight of happy Boosters who promptly gravitated to the new polo club while The Oxford Polo Club returned to a members' venue.  In 1998 the Booster club followed The Villages team to Barbados and established a reciprocal tradition that continues to this day.

Since its beginning, The Villages Polo Club spectator area has grown from a tent to a one floor area (near today's bathrooms and VIP area) followed by a second, then a third level, a stadium and additional fields and facilities.  The Booster Club, which had grown to over 1600 members by 2000, enjoyed games, parties, classes and field trips as determined by the Booster Board.  Monthly meetings held during the spring and fall season, featured classes taught by polo players, so that members could become educated and involved with the sport.  Those classes included 101 - Into to polo, 102 - The Ponies, 103 - Strategies and 104 - Rules and Fouls.  Eventually, the Polo Club staff decided to offer Polo 101 to all residents, while the advanced classes remained exclusive to Booster members.

The Booster Club, in addition to the advanced classes, offers a variety of other events exclusive to its members, such as, field trips to The International Polo Club in Wellington, The Sarasota Polo Club, The Grand Oaks Resort, The Florida Horse Park and Port Mayaca; along with visits to Tato's Mallet factory and store, The Tackeria and the Museum of Polo & Hall of Fame.

In 2023, the Villages Booster Club was informed that it had to rename and was no longer authorized to use "The Villages" in its name. The Board Members put their heads together and narrowed down a list of potential names to the fun "Pony Up Polo Boosters". The term "Pony Up" is used when its time to get on your horse, much like the military's "Mount Up". The Board also decided to go with the plural "Boosters" as there are so many of us. The Pony Up Polo Boosters is now looking forward to the next 30 years of enjoying and supporting Polo in The Villages.

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