No Matter How Many Times I Fight Him, I Can't Beat This Guy

[Scypion]

Jackie Callura (NBA Featherweight Champion in 1943) was stopped 3 times by Phil Terranova, twice for the NBA Featherweight title.

[HyacinthusTurnipseed]

Toshiaki Nishioka fought Veeraphol Sahaprom 4 times, losing a decision, drawing twice then losing a decision again. Maybe not fair to say he could never beat him but still , kinda rare to see someone fight the same guy in world title fights more than three times without winning once, especially after 2000.

[Scypion]

Sal Bartolo twice beat Phil Terranova in NBA Featherweight Championship fights in 1944.