Micheel is right.
The #3 connection is Medinah #3. All of those players finished second in a major there. In order, 1949 US Open, 1975 US Open, 1990 US Open, 1999 PGA, 2006 PGA.
(Question #3, was that a subtle hint?)
Number 5 just immediately screams "2003" so I narrowed it down pretty quickly to him or Ben Curtis.