Oldest and youngest players each of the big 3 have played against so far in their careers

[clout]

Oldest:

Federer played against Agassi (born in 1970) quite a bit earlier in his career but I'm not sure if Fed ever played against someone born in the 1960s

Nadal played Agassi twice at the beginning of his career as well and I'm quite positive AA is the oldest opponent Rafa has ever went up against

Djokovic played Moya (born in 1976) a few times at the start but I know he never played Agassi. If I had to guess, I'd probably pick Moya for this one

Youngest:

I think Shapo (born in 1999) was the youngest player Fed has ever faced as I don't think Fedr has ever played someone born after 2000 yet

Alcaraz (born in 2003) is now the youngest opponent for Rafa I'm 100% certain of this one. Before this year, it was Sinner at RG

Djokovic played Sinner (born in 2001) just last month in Monte-Carlo as well. Before this year, it was probably Shapo.


Most of these are only educated guesses though, if anyone actually has info on this feel free to put it in this thread

 

[Moose Malloy]

Didn’t research thoroughly, but Federer played Pozzi(b. 1965)

 

[clout]

Didn’t research thoroughly, but Federer played Pozzi(b. 1965)

Interesting! Certainly wasn't aware of that. Pozzi must've been a really old guy in that matchup then as he would've been in his mid-30s or older if he played Fed when he was a teen

 

[Deleted member 780630]

As said above, Pozzi was the oldest Federer played. There's also Pioline and Clavet who were born in 1969 and 1968 respectively, and Larsson and Fromberg who are one month and one day older than Agassi respectively.

Oldest Djokovic played was Santoro. Also played quite a few players older than Moya, with Henman and Rusedski being the most notable.