"If he misses another season for injury, we can apply for a sixth year," (VT compliance director Tim) Parker said. "As soon as they miss the second season for reasons outside their control, at that point they can apply for it. As a practical matter, we usually wait until sometime deep into their fifth year [because some athletes aren’t sure they want to return to college for a sixth year]. You can apply for it as soon as that second season is missed, even if it’s not in the fifth year."
— Why Darren Evans will not get a medical redshirt for this season According to the Richmond Times-Dispatch's Darryl Slater, Darren Evans can't apply for a medical redshirt for this season because he has already used his redshirt. If he misses another season due to injury (like Kenny Lewis likely will or Toney Baker), then he can apply for a sixth "medical hardship" year.