In the fall of 2009, Owner and President Andrew Starke announced the inception of the California Winter League. The California Winter League flourished in its first season in 2010, with over 50% of the players receiving spring training offers. With almost twice as many players in 2011, over 60% received offers. In 2012 the California Winter League expanded to five teams and had over 50% of players receive offers. In 2013 the California Winter League grew to 156 players and had 8 teams in the league, playing 3 to 4 games a day between two facilities. The league continued its success with 50% of the players in the league getting professional contracts. Three of contracts were to MLB organizations, Rangers, Diamondbacks and Phillies. In 2014, the California Winter League saw 60+ players get signed professionally, with a couple of players getting private workout invitations from the Texas Rangers. The 2015 season represented more growth, both from a player standpoint (200+) and from a complex standpoint (new all-turf auxiliary field). The California Winter League also entered a two-year agreement with the Frontier League that guarantees 31 roster spots for players coming directly out of the CWL. Despite the 31-player signing minimum, the Frontier League signed 50 players out of the league, proving that only the best players come from the California Winter League. Both parties in the agreement hope to send even more players to play professional ball in 2019.

In 2019, the California Winter League will continue to grow by having 300+ players join the league and play for professional contracts. The new agreement with the Frontier League makes the CWL the “exclusive” winter league of the Frontier League.