User blog comment:KrazyKeke/Who's Better: Ichigo or Byakuya?/@comment-4326112-20130309231603

Well it was purely circumstantial that Ichigo won. While Ichigo is a formidable, natural fighter, Byakuya has trained over a century for his abilities and can easily adapt his strategy in fighting Ichigo. After all, Ichigo lost to him the first time they encountered (he looked like a wimp that time XD) and then he would've died the second time, had it not been for Yoruichi, and technically without his Hollow interrupting the third battle, Byakuya would've beat him.

So yeah, unless there was a form of Plot Armor protecting Ichigo (which pretty much there is most of the time) Byakuya would beat him hands down every time.