LL cool J vs Talib Kweli - Neither are battle emcees .. But probably Talib for having a bigger lyrical ability overall.
Big daddy kain vs 50cent - 50 Cent, they both suck lyrically though.
KRS-1 vs nelly - KRS-1, easily. This already happened
Run Dmc vs Big tymers - Run DMC, easily. What the fuck
Craig Mack vs Lil wayne - Craig Mack, easily.
Public enemy vs Def Squad - Def squad, easily. PE aren't battlers.
Tupac vs Nas - Tupac, easily. Nas isn't much at battling
B.I.G vs Eminem - Eminem, easily. He's been battling all his life
Fresh Prince vs Fat Joe - lmao, Fat Joe easily
Eazy-E vs Keith Murray - Keith Murray, more aggressive
Ice Cube vs Ludacris - Ludacris, better lyrics

Shitty matchups