So, besides the '98 commemorative book, it looks like the spring game program is from 1988 and the Fan Pack envelope is from around 1992. The picture on the spring game program #33 is Keith Delong, All-American linebacker, to the left of that written upward it looks to me like Harry Galbreath an All American on the OL but I thought he finished in '87. Terry McDaniel- also an All American at CB is on the helmet. He finished in '87 too. Mark Adams TE in on there on the top right side, the upside down ones I can't make out or the faint one that's covering Delong's jersey.
The Fan Pack envelope has Kevin Mays, Vol OL patriarch, in the middle. I see Shawn Summers DB, Tom Hutton the punter #43, JJ Surlas DL is upside down at the top, I think that's Cory Fleming, future Cowboy, over the "Vols" return address.
The other envelope I would also put at around 1988. I see Shon Walker LB bottom left, I think Marion Hobby future all SEC DL just signed "Hobby" in green bottom middle, future first round draft pick OL Charles McCrae is on there, Lee Wood (I was lab partners with him in Geology) wr, Adam Epstein k, Dirk Borgeone who, I think, at one time held the record for longest FG by a high school kicker is on there and Carey Bailey DL is in the middle. I'm pretty sure you can look up the rosters by year at the UTAD site and match the numbers with the signatures better. Those are just ones that I could read that popped out. Those are some great old names and great VFLs!