Answers revealed in the comments.
GAME 1
William Jennings Bryan was a Democratic U.S. presidential candidate three times, losing to two different people. Name either of the two Republican presidents to whom Bryan lost a presidential election.
GAME 2
Two different private universities have won the NCAA Division I Women’s Basketball tournament since the tournament expanded to include 64 teams. Name one of those two private universities.
hebspeaks 
Game one answers:
William McKinley (1896 & 1900)
William Howard Taft (1908)
Game two answers:
Notre Dame (2001)
Baylor (2005 and 2012)