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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
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