The "Weymouth Challenge Cup" presented to the DCGU by Weymouth Golf Club to be presented each year to the boy with the best net score at the Boys Championship.

Winners:

• 2024: Max Dunn (Weymouth)
• 2023: Andy Su (Broadstone)
• 2022: Ben White (Ferndown)
• 2021: Toby Trott (Weymouth)
• 2020: Jake Moore (Ferndown)
• 2019: Jacob Tidswell Parkstone
• 2018: Ollie Griffiths Sherborne
• 2017: Sam Trott Weymouth
• 2016: Jacob Tidswell Weymouth
• 2015: Dominic Dunstan Ashley Wood
• 2014: Billy Hathway Weymouth
• 2013: Alex Fernandez Parkstone
• 2012: George Long Parkstone
• 2011: Harry Mitchell Ferndown
• 2010: Tom Robson Weymouth
• 2009: Ryan Warrener Broadstone
• 2008: Robbie Busher Rushmore 
• 2007: James Wythe Ferndown 
• 2006: L Mills Queens Park 
• 2005: D J Smith Parkstone 
• 2004: L Rogers DG&CC