Steven Stamkos began his post-season career at the age of 9. Not only did he win the OHL Cup with the Markham Waxers in 2006, he also won the Coronation Cup of the Greater Toronto Hockey League in 1999 -- alongside teammate PK Subban. Stats for these games are difficult to find, but let's assume that Stamkos had a big hand in both of these cup victories.
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When Stamkos played with the Sarnia Sting of the OHL in 2006-07 and 2007-08, his two seasons garnered him a total of 13 playoff games played, 14G/3A for 17 points.