Lorewise, yes, it seems he fears his other selves from different dimensions or some shit.
Here, it probably means the times he died after casting False Promise on himself or PA herself killing him with the blades he gave her. Either that or Valve has got to answer some questions.
Oracle pls.
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http://www.dota2.com/oracle/day3?l=english
pa has to kill heroes oracle fears the most
he fears himself?
"oracle has slain oracle 19480 times"
wat