Bob Reading, Ron Steele, and Chuck Breeding met many times in the winter of 2007 to create a team that would play regular season games and tournaments in the Region. They acquired the use the high school’s gym for Winter Tryouts and signed 27 boys for the newly formed organization and got many local businesses and the Mark Rypien Foundation to donate money to support the team.
In the 2007 season, Kent Island Select formed two teams and entered the Anne Arundel County League 14U A and B Divisions. Each team took second place. The teams participated in the 27th Annual Essex Express Tournament in Baltimore and played in the Bases Loaded 13U Tournament at the Cal Ripken Complex in Aberdeen, Maryland and the BPA Mid-Atlantic 13U and 14U Regional Tournaments in Bowie, Maryland. The two teams participated in additional tournaments in Delaware, Annapolis, Harford, Howard, and Southern Maryland.
In 2008, they expanded slightly and had a 14U team and a 10U team that entered the Anne Arundel County League. The 14U team won the County Championship. They were runner-up in the Essex Tournament and played in other regional tournaments. They also participated in the week long Tidal Wave Tournament in Myrtle Beach, South Carolina and played teams from across the country and Canada. The 10U team came in fourth place in the Anne Arundel County League and played in one tournament in Southern Maryland.
In 2009, Kent Island Select Baseball had two teams. The 12U team entered in the Anne Arundel League again and the 16U team played in the newly developed NABF Wooden Bat League. They qualified for the Wooden Bat Regional. They also played tournaments in Maryland, Pennsylvania, and in Orlando, Florida at the Disney Wide World of Sports Complex. The team consisted of players from three different high schools. The 12U team placed 5th in the Anne Arundel League and played in the Essex Tournament and at the Ripken Complex in Aberdeen.
In 2010, Kent Island Select Baseball had a 12U and a 16U team and played league play across the bridge in Anne Arundel County again for the 12U's and in the Wood Bat League also. The 12U team finished in fifth place, as did the 16U's. The 12U team participated in the Memorial Day Shootout in Lusby, MD and finished in 2nd place in the Silver Division, winning two games. They also were runner-up in the First Annual Deale Baseball Tournament. Liam Christenson, Bryce Wygal, and Danny Reading were named to the All-Tournament Team!
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