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Growing up in Middlesbrough's Pallister estate, Downing has always naturally supported Boro since a very young age. He joined the club as a schoolboy and became one of the most promising young footballers at the club's academy. He made his first team debut on 24 April 2002 in an away league fixture at Ipswich Town, fulfilling a boyhood dream.
The two seasons that followed were to be the most frustrating of his career, only making three appearances in each due to the fine form of left-midfielder Bolo Zenden. In 2003 he was sent out on loan to Sunderland. When he returned, an injury crisis at the Riverside Stadium meant that he was able to break in to the first team.
In 2004-2005 Downing scored six goals in 49 appearances, drawing the attention of many with an array of impressive performances. In February 2005 he was rewarded, making his international debut in England's friendly clash against the Netherlands.
The following season was a major disappointment for Downing, spending five months on the sideline due to a devastating knee injury. He played on at Middlesbrough, becoming the second longest serving player in the club's history.
In 2009, Downing made a £10 million move to Aston Villa, following a disappointing season at Boro in which the club were relegated. He went on to make 63 appearances at Villa Park, scoring nine goals before he became Liverpool's third major signing of this year's summer transfer window after completing a £20 million transfer.