Roberts spent nine years at Prenton Park and made almost 270 league appearances for the club. It was whilst at Tranmere that Roberts came closest to winning a major domestic honour, as he was part of the Tranmere side which reached the club's first ever major cup final, the 2000 Football League Cup Final, where they narrowly lost out 2–1 to Premier League side Leicester City whilst they were still in the second tier. After a midtable finish that campaign, however, Roberts first full season at the club saw Tranmere relegated in bottom place.