West Ham's involvement in the UEFA Intertoto Cup meant that they would have their shortest close-season in history. Only 62 days had passed since the last game of the previous season before West Ham took to the field against Jokerit of Finland.

West Ham had already played four games before the Premier League season began, and this match-fitness head-start on the rest of the division would see them in third place after five games.

Although they lost in the first leg of the Intertoto Cup Final at home to Metz 1-0, West Ham managed to win the return leg 3-1 two weeks later and ensure UEFA Cup football.

Harry Redknapp regarded this result as his greatest night as West Ham's manager: "That was a great performance and a great day for West Ham, to win the Intertoto Cup and to be in the UEFA Cup and turning in such an outstanding performance against a good French team, to go over there and play so well and win 3-1. We took great support over to France and they enjoyed their day. Yeah, I think that was special. That was a real good day for me and West Ham's history."

Frank Lampard was West Ham's top European goalscorer with four in ten games. He, along with Trevor Sinclair, Paolo Di Canio and captain Steve Lomas, were ever-present in West Ham's European campaign.

After making only one substitute appearance in West Ham's first Intertoto Cup game, Ian Wright was loaned to Nottingham Forest. Later in the season he would sign a permanent deal at Celtic.

On 15 December 1999, West Ham played a League Cup quarter-final game against Aston Villa. The game went to extra time and a reserve player, Emmanuel Omoyinmi, was brought on as a substitute for Paulo Wanchope in the 113th minute. Unknown to manager Harry Redknapp, Omoyinmi had previously played in the competition for Gillingham, where he had spent time on loan earlier in the season, and was thus ineligible to play. Although the Hammers won the game on penalties, the game was replayed after the Football League upheld a complaint by Villa. West Ham lost the replay 3-1. The error eventually led to the resignations of club secretary Graham Mackrell and football secretary Alison Dowd: "Whatever happens, I'm responsible for administration here at West Ham United. The buck does stop with me," said Mackrell.

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Wikipedia