Great idea for a quiz. Needs updating though. You also need to at least treble the time. There are over 200 different answers.
Also, you need to look at the type ins for a few, Leicester manager in 15-17 requires full name, but his surname is accepted elsewhere. Similar issue with Boro manager 00-01.
Howard Wilkinson is listed as managing from 1998-1996. Graham is '96-'98. That's most definitely not correct. Unless Wilkinson's a time traveller. So... probably fix that?
Also, you need to look at the type ins for a few, Leicester manager in 15-17 requires full name, but his surname is accepted elsewhere. Similar issue with Boro manager 00-01.