The Pool was started in 1996 by Ray Hunt. Ray no longer runs the Pool, but he still participates.

The first year there were 12 teams entered. The entry fee was $50.00 and there were 3 cash prizes.

The entry fee went up to $100.00 in 1997.

1999 was the first year that a free entry for the subsequent year was awarded for finishing in last place.

Monthly prizes were first awarded in 2001. That year the entry fee went up to $130.00 where it has since remained. Originally there were 3 monthly prizes. That was increased to 4 in 2019 and then 5 in 2020.

In 2014 the PGA Tour introduced schedule changes that resulted in the golf season being split over 2 calendar years. In order for the pool to cope with this change it was decided that the results of all tournaments played prior to the Tour Championship, which is played in early January, would not be included in the Pool. As a result, the pool continued to start in January as it had always done in the past.

The 2019/2020 pool was cancelled in early March after the PGA Tour cancelled several tournaments because of the COVID-19 pandemic.

Due to the 2019/2020 cancellation, the 2020/2021 pool started in October. As a result, the number monthly pools increased to 10 and the number of monthly prizes was reduced to 3.

Beginning in 2023, the pool reverted to a January start. With the elimination of the Fall tournaments, the number of monthly prizes was increased from 3 to 5, as the monthly pools for October and November no longer existed.

The record for the most teams entered is 538 for the 2020/2021 season.