Which heavyweight champions fought the best fighter on the planet most often.

Charles vs Oma was in January 1951. Ring Magazine published rankings monthly. Their rankings in December 1950 were as follows:

Champion - Ezzard Charles
#1 contender - Joe Louis
#2 Lee Savold
#3 Joey Maxim
#4 Lee Oma
#5 Bob Baker
#6 Clarence Henry
#7 Rex Layne
#8 JJW
#9 Jack Gardner
#10 Rocky Marciano

 

Yeah I won’t die on that hill. Was going by yearly

 

No worries.

I think Charles was an elite, top tier, ATG. I have him #1 all time at LHW and have argued hard to defend that on this forum. I think he's the 5th greatest boxer of all time, regardless of weight.

It's just I've spent literally thousands of hours collating and analysing data to support my all time rankings. Taking it that seriously necessitated the consistent application of criteria, which for me, for my divisional rankings, meant each fight contributes to a fighter's resume at one weight only. I assign every fight each boxer I assess contested into one weight division only. On this basis, I have Charles #16 at HW. Which is still exceptionally good for my GOAT LHW.

 

Around where I have him as well.