I have a horrendous career record against osgonlz, considering how solid my programs have typically been. I don't remember the exact record, but I think I'm something like 3-13 against him. This includes a stretch in Crum where I went 63-1 in conference play over four season. In those four season, I was 3-1 against os. I'm 0-10 (I think, I'd have to check to be sure) in all other Crum/Naismith/Rupp meetings.
I think I lost nine straight against bhbum before I got my first win against him. I don't think I've played HD long enough to have 20 games against an individual coach, but those are the worst I can think of. The overall record is definitely not as bad, but I definitely know the feeling on the whole "look at this team I've built, seriously how am I not beating him?" level.