As Wigan settled into their new home at the JJB Stadium, Benson's side went 26 league games undefeated, before losing at home to Oldham Athletic on 7 January 2000, Benson picking up 2 Manager of the Month awards in the process.
Towards the end of the season Wigan lost their form and found themselves in the play-off final at Wembley against Gillingham.
A few days prior to the game, Benson had announced he was stepping down but remained to lead his team out at Wembley and ultimately a 3–2 defeat after being 2–1 up with only 7 minutes of extra time remaining.
Note: Flags indicate national team as defined under FIFA eligibility rules; some limited exceptions apply.
Note: Flags indicate national team as defined under FIFA eligibility rules; some limited exceptions apply.