Some sample questions from this category:
* 1999/2000: Arguably the most prolific team in Tranmere's history, as they made the Worthington Cup Final as a second tier side, before being beaten by Leicester City. How many then top flight sides did Tranmere beat in the Worthington Cup in the season?
* 1999/2000: In the FA Cup, Tranmere reached the quarterfinal of this competition as well, but what was peculiar about their Fourth Round tie?
* 2000/2001: How many then Premiership sides did Tranmere defeat in the season in the FA and League Cups?
* 2001/2002 was Tranmere's first season outside of the second tier since the start of the 1990s. The same team knocked them out of both major competitions with two 4-0 scorelines. Which team was this?
* 2003/2004: In their quarterfinal tie, they faced eventual runners-up Millwall, and although Tranmere eventually got beaten 2-1 at home in the replay, which Millwall player had his penalty saved by John Achterberg in the 0-0 draw at The New Den?