This was Bolton's second appearance in the second tier play-off final; they had beaten Reading 4–3 after extra time in the 1995 final. Watford were making their first appearance in the second tier play-off final, but had lost to Blackburn Rovers in the 1989 play-off semi-finals. Bolton were aiming to make an immediate return to the top tier of English football having been relegated from the Premier League in the 1997–98 season on goal difference. Conversely, Watford were seeking back-to-back promotions, after ending the previous season as champions of the Second Division (third tier). They had been outside the top tier for eleven years. In the two regular season meetings between the two clubs, Watford had won both, defeating Bolton 2–1 at the Reebok Stadium in October 1998 and 2–0 at Vicarage Road the following April. Graham Taylor, the Watford manager, was making his first visit to Wembley Stadium since September 1993 in his last game as England manager. Reflecting on Watford's appearance at the national stadium in the 1984 FA Cup Final, he suggested: "There are two ways to go to Wembley. You either go as Watford did against Everton... just happy to be there. Or you go to win." Elton John, Watford's chairman, also spoke similarly of the 1984 final: "Yes, we desperately wanted to win... but there was something about getting there which was a victory in its own right for a relatively small club like ours". He went on to suggest that both Taylor and his team had an "overwhelming determination" to succeed in the play-off final.