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I recently shared some Rivalry Week photos on social media, which prompted lots of questions about this Whitby tradition.
A huge thank you to Henry Dewit and Wade Szilagyi from the amazing Vintage Whitby Facebook group for helping to compile this information.
Rivalry Week is a longstanding competition between Henry Street High School and Anderson CVI.
It got its start in 1968 as a one-day football game established by Mayor Des Newman, with the Mayor’s Cup trophy awarded to the winner.
The Mayor’s Cup ended in 1984 when Anderson CVI ended its football program. The idea was reignited in 2009 with the inaugural “Rivalry Week” that saw teams from Anderson and Henry face off in a weeklong series of hockey, basketball and volleyball games, with the Mayor's Cup awarded to the school that won the most events during the week.
Anderson CVI was the first winner of the Rivalry Week Mayor's Cup.
Rivalry Week also encompasses other activities that promote school spirit, such as themed dress-up days and school decorations.
Over the years, there have been some pretty memorable games, including the 2011 hockey game played at Tribute Communities Centre in Oshawa that saw the Anderson Raiders win 3-2 in a shootout.Bottom of Form
In 2013, the Henry girls' volleyball team was down two sets and pulled off an incredible comeback, winning the next three sets to secure the Mayor's Cup.
Then there was the 2015 boy’s basketball game that went into double overtime, with Anderson eventually emerging victorious, winning 72-68 in a game still talked about today.
Congratulations to Henry for winning the 2025 Mayor’s Cup – it was so much fun to attend some of the games and watch crowds of students dressed in school colours cheer for their school.