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Between January and May 2018 Lewington temporarily worked in a player-coach role for the club under then manager Dan Micciche. Lewington achieved his 600th league appearance and 700th appearance in all competitions for the club in January 2019 in consecutive games against Crewe Alexandra and Grimsby Town.

On 3 May 2015, Lewington scored twice and assisted two further goals as the Dons defeated Yeovil Town 5–1 on the final day of the season to earn their first promotion to the Championship.

Lewington scored his only goal of the 2013–14 League One season in the last minute of a 3–2 victory over Stevenage at Broadhall Way. The 2–2 draw with Rotherham United at the New York Stadium on 26 April 2014 saw Lewington make his 500th appearance for Milton Keynes Dons in all competitions. To celebrate his 500th appearance for the club, supporters of Milton Keynes Dons got together for the last home game of the season against Leyton Orient, and wore as much orange as possible (due to Lewington's hair colour). This campaign was dubbed "Orange4Lewie" and gained some publicity from Twitter, Facebook and other social media.

On 20 May 2014, Milton Keynes Dons announced a testimonial match against Nottingham Forest would be played in honour of Lewington's ten years of service for the club. The match was played on 27 July 2014 at stadium:mk although 4,121 attended the game, of whom 1,286 were from Nottingham Forest. At the time of his testimonial, Lewington had amassed over 500 appearances in league and cup competitions for Milton Keynes Dons.

On 2 December 2012, Lewington captained his side against AFC Wimbledon in their highly publicised first meeting. On 12 January 2013, Lewington made his 400th league appearance for Milton Keynes Dons against Bury.

He received the MK Dons captaincy after the departure of Keith Andrews to Blackburn Rovers in August 2008. On 21 March 2011, Lewington led his team to a 1–0 victory over promotion rivals Peterborough United. The Dons reached the play-offs but were defeated by Peterborough.

Born in Kingston upon Thames, London, Lewington made his Wimbledon first team debut on 5 April 2003, coming on as a last-minute substitute for Alex Tapp in a 4–2 First Division defeat to Sheffield Wednesday at Hillsborough, his only appearance of the season.

On 1 November 2003, he made his first start, in a 2–1 win over Bradford City at the National Hockey Stadium, their first victory in Milton Keynes. He scored his first goal on 26 December in a 3–0 win away to Reading at the Madejski Stadium, heading Adam Nowland's cross for the second of the game. Lewington was sent off for violent conduct near the end of the team's 0–3 home defeat to Coventry City on 21 February 2004. At the end of the season, Wimbledon were relegated.

Having moved to Milton Keynes in 2003, Wimbledon were relaunched in 2004 as Milton Keynes Dons, in the newly renamed League One. Lewington almost moved to Huddersfield Town in 2005 in an exchange deal involving Pawel Abbott, however Abbott chose to stay at Huddersfield thus ending their interest. As of January 2020, Lewington is the only former Wimbledon player at Milton Keynes Dons.

Dean Scott Lewington (born 18 May 1984) is an English professional footballer who plays as a left-back for League One club Milton Keynes Dons where he is currently club captain. He is the club's longest serving player.