From the days of Frankie Hayes, who played for Pennington in the 1920s and who went on from Pennington to play for the Philadelphia Athletics and their legendary coach Connie Mack, to Coach Poore’s 1963 team that defeated Lawrenceville 2–1 in a home thriller, to the mighty Pennington teams that consistently won or vied for Penn-Jersey League titles and Prep State Championships in the 1970s and 1980s Pennington baseball has enjoyed longstanding popularity at the School. More recently, the 2017 and 2018 teams have enjoyed fine seasons. The 2017 team lost in the NJISAA Prep B championship while in 2018 Pennington secured the first Prep B title in 33 seasons as they won a 2-1, extra-inning thriller over Gill St. Bernards School. Several baseball alumni have taken their games to the DI or DIII levels at schools including Lafayette College, Dickinson College, University of the South, Lehigh University, Hofstra University, University of Alabama, Lebanon Valley College, Skidmore College, and Vassar College, among others. Pennington’s baseball program is alive and well as today’s team play on the very same Heritage Field. Facilities include batting cages, dugouts, and a digital scoreboard.  The baseball program also makes preseason trips to Florida for practices and scrimmages during the School's spring break.