Senior Player of the Year

• 2006: Dr. George Pirie, Valley CC
• 2007: Paul Quigley, Swansea CC
• 2008: Dr. George Pirie, Valley CC
• 2009: Paul Quigley, Metacomet CC
• 2010: Paul Quigley, Swansea CC
• 2011: Dr. George Pirie, Valley CC
• 2012: Paul Quigley, Swansea CC
• 2013: Dave McNally, Foster CC
• 2014: Dr. George Pirie, Valley CC
• 2015: Paul Quigley, Swansea CC
• 2016: Paul Quigley, Swansea CC
• 2017: Dr. George Pirie, Valley CC
• 2018: Paul Quigley, Green Valley CC
• 2019: Bruce Heterick, Metacomet GC
• 2020: Darren Corrente, Wannamoisett CC
• 2021: Darren Corrente, Wannamoisett CC
• 2022: Darren Corrente, Wannamoisett CC
• 2023: David Marshall, Quinnatisset CC
• 2024: David Marshall, Quinnatisset CC