Lots. It wasn't catastrophic at the time -- in most cases. (There were a few!)

I remember when HP was trying to test their DC in Germany, they rolled the computers (and the VMs) up, and then back, but the DC locks, well, locked, and the staff couldn't get in to access the computers to resolve any RT logging info spewing out. Fun times.

Many of the Y2K problems were handled annually, monthly, weekly, daily, hourly, minutely and secondly well in advance of "the deadline".