As far as collabs, they was 1-1 (while biggie was alive) biggie outshined jay on Brooklyn's finest, jay did better on I love the dough.
As far as overall, jay imo has never left earth lyrically like biggie did on life after death.
Btw I remember reading a interview where biggie actually did admit he wasnt the best at the moment but the 2 lyricist he claimed was better than him was method man and nas.