You can apply for a medical redshirt after the season in which the player is injured if the injury occurred before around the 4th game of the year. Oldroyd was injured in game3 of his freshman year and lost for the season so he should qualify? The new regular redshirt rule is 4 games played, injured or not.
You’re probable thinking of some players who’ve applied for a 6th year of eligibility after their senior year after suffering two season ending injuries. Byu’s has had a few of those. Mike Hague. Matt Hadley. Pututai is another who might have a shot to apply for a 6th year if eligibilty (if he wants to) after this year. He lost a full year as a Sophmore and got the medical redshirt. He was injured last year as a junior in first half of the 4th game, early in the season. He already used a medical redshirt so he’s a Senior this year, but with the two season ending injuries could very well qualify for a 6th year.