Dean Brill

Oldham Athletic On 1 July 2009, Brill signed a two-year contract with League One club Oldham Athletic. He was released by the club in May 2011.

Barnet After trials at Yeovil Town and Barnet, Brill signed for the latter on a one-year contract. He kept a clean sheet on his debut in a 1–0 win away to Morecambe. He was released by the club in May 2012.

Return to Luton Town After spending three weeks on trial during pre-season with former club Luton Town, who were in the Conference Premier, Brill signed a two-year contract with them on 31 July 2012. He made 12 appearances in 2012–13,

Inverness Caledonian Thistle In July 2013, Brill signed on loan for Inverness Caledonian Thistle until January 2014. He debuted on the opening day of 2013–14 in a 3–0 win at home to St Mirren, keeping his first of three consecutive clean sheets.

Between May and September 2014, Brill did not let a single goal in, enabling Inverness to achieve a club record of 616 minutes without conceding a goal. Later in the season, Brill suffered an injury which kept him out for a few matches. Worse was to follow, as he sustained a dislocated knee only minutes into his comeback game. This prevented him making any first-team appearances in 2015–16 and he was released by the club in May 2016.

Motherwell Brill signed for Scottish Premiership club Motherwell on 27 June 2016 on a one-year contract. He left the club on 27 January 2017, having failed to make an appearance.

Colchester United On 31 January 2017, Brill signed for Colchester United on a contract until the end of 2016–17. He left the club at the end of his contract after failing to make a first-team appearance.

Leyton Orient Brill joined newly relegated National League club Leyton Orient as a goalkeeping coach on 3 August 2017. Following Steve Davis' sacking as head coach on 14 November, Brill was named interim head coach alongside Ross Embleton. After Justin Edinburgh was appointed head coach later that month, Brill became a member of the playing staff, making his debut for the club on 2 December in a 1–0 away defeat to Solihull Moors. He signed a two-year contract extension in February 2018 after he kept five clean sheets in 14 appearances up to that point in 2017–18. He finished the season with 29 appearances for Leyton Orient and was replaced as goalkeeping coach in July, allowing him to focus on his playing career. The following season, Brill was ever-present in league competition and kept 24 clean sheets in all competitions, equalling the club record, as Leyton Orient won the National League title and promotion to League Two. Ahead of the 2019–20 season, Brill signed a one-year contract extension with the club. After making 20 appearances in the first half of the season, with 19 of those appearances coming in the league, he sustained an injury in late December 2019 and announced his retirement from playing on 24 January 2020 to rejoin the club's coaching staff. and interim head coach on 14 November before returning to playing. He was appointed first-team coach at Leyton Orient in January 2020 and head of goalkeeping in July 2020. He left Orient in June 2021 to become a goalkeeping coach at Tottenham Hotspur's academy where he became head of academy goalkeeping in July 2022. In July 2025, Brill was promoted to first team assistant goalkeeping coach.

Career statistics

Honours Luton Town Football League Trophy: 2008–09

Inverness Caledonian Thistle Scottish Cup: 2014–15 FA Trophy runner-up: 2018–19

Individual Luton Town Young Player of the Season: 2006–07