Stewart Downing began his career at Middlesbrough where he was touted as one of the most promising graduates of their academy. His first team debut arrived in April 2002 in a Premier league game away to Ipswich Town. He made two more appearances that season before managing to score his first goal for the club in the 4-1 League Cup victory over Brentford in the following campaign. However, Downing again only made two more first team appearances that season. He was loaned out to Sunderland for the first part of the 2003/04 campaign where he made seven appearances scoring three goals in the process. It was on his return that he made his impression after being forced into the first team due to other injuries. The 2004/05 season saw Downing establish himself as a first team regular with 49 appearances including six goals and numerous assists.
A knee injury saw Downing sidelined for five months at the end of 2005. However, he returned to play a part in the club's fantastic UEFA Cup run at the end of the 2005/06 season. More consistent performances over the next two seasons saw him often linked with transfers to more illustrious clubs but he stayed loyal to Middlesbrough. The 2008/09 campaign saw Middlesbrough undergo their best start to a season for some time as they climbed to 8th in the table. However, a terrible winless run saw them sink into the relegation zone where they stayed until the end of the season. Downing ended the season with no league goals and a move away looked inevitable. Although he is currently injured for a couple of months, Downing signed a four year deal with Aston Villa for a fee of £10 million.
A knee injury saw Downing sidelined for five months at the end of 2005. However, he returned to play a part in the club's fantastic UEFA Cup run at the end of the 2005/06 season. More consistent performances over the next two seasons saw him often linked with transfers to more illustrious clubs but he stayed loyal to Middlesbrough. The 2008/09 campaign saw Middlesbrough undergo their best start to a season for some time as they climbed to 8th in the table. However, a terrible winless run saw them sink into the relegation zone where they stayed until the end of the season. Downing ended the season with no league goals and a move away looked inevitable. Although he is currently injured for a couple of months, Downing signed a four year deal with Aston Villa for a fee of £10 million. Downing moved to Liverpool in 2011 staying for two seasons before moving to West Ham United in 2013.