Originally Posted by timnz
1920's great Tilden played P. Gonzales and lost in the early 1960's (Tilden was around 60 at the time)
P. Gonzales beat Jimmy Connors in the early 1970's
Jimmy Connors lost of Agassi in the late 80's
Agassi played Federer a number of times in the early-mid 2000's
We could be starting something here.