Allardyce was appointed manager of Bolton Wanderers following Colin Todd's departure, who had resigned in protest at the sale of Per Frandsen as the club attempted to raise funds for the new Reebok Stadium. He inherited a talented squad, which included Eiður Guðjohnsen, Jussi Jääskeläinen, Mark Fish, Claus Jensen, Dean Holdsworth, Bo Hansen, Michael Johansen, and Ricardo Gardner. However he was forced to sell Andy Todd, son of Colin Todd, after he broke assistant manager Phil Brown's jaw in a team bonding session. Despite being in the bottom half of the table when he took over, Bolton reached the 1999–2000 Division One play-offs, losing to Ipswich Town, and had an eventful run to the League Cup and FA Cup semi-finals, only missing out on the 2000 FA Cup Final after a penalty shoot-out defeat to Aston Villa. He blamed referee Barry Knight for the play-off defeat, who he accused of being biased against Bolton. Allardyce was rewarded for turning the club around with a ten-year contract, though the terms of the contract only entitled him to a one year's compensation pay if he was sacked.