So, February 8th of 2021. Federer is currently 55 weeks behind Connors here. He would need to earn somewhere around 600 ranking points to achieve this all of next year. We shall see.Federer is currently 95 behind!, Fed will need to be Top 100 by 08/02/2021 to surpass him.
After he passes Connors, he'd have the longest career of any significance of anyone in the open era.
The only player who's done anything close to what he's doing now is Rosewall, and Federer is getting pretty deep into his career too.