Chris Chelios is the oldest active NHL player who has not won a Stanley Cup. Chelios plays for the Detroit Red Wings.
It might be the Stanley cup.
My guess would be Dave Andreychuk who was 40 years 7 months when the Lightning won the Stanley cup in 2003-2004 but I am not certain of that. Andreychuk was also the oldest player to ever play his first Stanley cup finals game.
Every player on the active roster, coaches, and owners
The Stanley Cup was donated in 1893, making it the oldest trophy in professional team sports. The Grey cup was donated in 1909.
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Nicklas Lidstrom, Thomas Holmstrom, Kris Draper, and Kurt Maltby all have four Stanley Cup rings. (1997, 1998, 2002, and 2008).
Each member of the winning Stanley Cup team gets to spend 24 hours with the Stanley Cup.
The Stanley cup
The St. Louis Blues
The oldest player in a soccer World Cup (and oldest player to score in the World Cup) was Roger Milla of Cameroon aged forty two years old!