TIL Sergei Federov, Alternate Captain of the Detroit Red Wings, dated 16 year old Anna Kournikova in 1996 after winning the Stanley Cup.

https://vault.si.com/vault/1998/03/30/annatude-at-16-thats-what-russian-phenom-anna-kournikova-hasin-addition-to-talent-sex-appeal-and-a-good-friend-with-a-stanley-cup-ring

https://www.reddit.com/r/todayilearned/comments/150z221/til_sergei_federov_alternate_captain_of_the/