Answers to these questions are in the comments.
GAME 1
La Navidad was a settlement built in 1492 by Christopher Columbus from the remains of the Santa Maria, and was the first European settlement in the New World during the Age of Discovery.
On what island was La Navidad located?
On what island was La Navidad located?
Still from Looney Tunes short “Hare We Go.”
GAME 2
Three Olympic medal-winning boxers have competed on the ABC reality TV competition Dancing with the Stars. Name two of those three boxers.
hebspeaks 
Game One answer: Hispaniola
Game Two answers: Sugar Ray Leonard
Evander Holyfield
Floyd Mayweather Jr.