Sheringham then dropped down a division to West Ham United in the Football League Championship, and was the division's third-highest goalscorer with 20 goals (21 in all competitions) – one of the highest scoring seasons of his career. He won the Championship Player of the Season award, and helped the "Hammers" reach the 2005 Football League Championship play-off Final where they beat Preston North End to return to the Premiership after two seasons in the Football League. At the end of the 2004–05 season, Sheringham's one-year contract expired and he agreed to sign on for another season, this time back in the Premiership, at Upton Park. After a second-half appearance against Charlton Athletic on 2 April 2006, Sheringham joined a small group of footballers, including Les Sealey, John Burridge, Gordon Strachan and later Ryan Giggs, who have played top-flight football while in their 40s. On 19 August 2006, he became the oldest outfield player in the history of the division, at 40 years 139 days. Sheringham signed a contract to play for West Ham until the end of the 2006–07 season, and was a player at the club after his 41st birthday. On 13 May 2006, Sheringham became the third oldest player to appear in an FA Cup final, at 40 years and 41 days old. The game ended 3–3, with Liverpool winning the trophy in a penalty shootout. Sheringham was the only West Ham player to convert his kick as Liverpool won the shootout 3–1. On 26 December 2006, at the age of 40 years and 266 days, he beat his own record for oldest Premiership scorer, with the goal in a 2–1 defeat to Portsmouth. On 30 December 2006, he broke the record for oldest Premiership outfield player once more, playing in the 1–0 defeat against Manchester City, aged 40 years and 270 days. Sheringham also appeared in 11 FA Cup, League Cup, and UEFA Cup games for West Ham, scoring two goals.