Friday afternoon picture quiz

[Fantastic News of Boro]

There are two separate seasons being discussed here.
The photo of the Leeds game is from the 92/93 Premier League season.
The Wilkinson facts are from the 91/92 promotion season.

Ripley was here during the promotion season 91/92.
He left for Blackburn in the summer before the 92/93 season.

Rofesleg 5 extra special FNOM bonus points for providing such clarity about the question and 2 more for the fact that Randy ‘Rudolph’ Crafton, or Beak, was a close personal friend of yours. That makes 7 altogether. Well done!