Reading Dickie joined
Reading as an eight-year-old. In the
2013-14 season, Dickie made 34 appearances playing every minute of the
FA Youth Cup campaign for the under-18s where he scored in the semi-final against
Fulham. Dickie signed his first professional contract with Reading on the 3 July 2014. On 24 December 2014, Dickie made his first loan to
Basingstoke Town until 25 April 2015. He made 24 appearances for Basingstoke and helped them to reach the Conference South play-offs but it all ended in defeat over two legs against
Whitehawk. Dickie only made one appearance for Reading when he came on as a substitute and played 45 minutes in the last game of the
2015-16 season against
Blackburn Rovers. On 9 May 2016, Dickie was one of 15 Reading youth-team players offered a new contract by the club, with confirmation of his new deal being signed coming on 1 July 2016. After the second loan spell at Cheltenham Town came to an end, Dickie was involved with under-23 team and captained the side to the
Premier League Cup final during the latter part of the
2016-17 season which ended in defeat against
Swansea City. He also provided a goal against
Norwich City in the semi-final.
Cheltenham Town (loan) On 20 August 2015, Dickie joined
Cheltenham Town on a one-month loan deal, making him Cheltenham's 17th signing of the window. The manager
Gary Johnson was pleased with the signing as a Dickie suffered a slight injury in pre-season which delayed the process. Two days later, on 22 August, Dickie scored the winner on his debut in a 2–1 win over
Barrow. Dickie's loan deal was then extended on for an additional month on 23 September, on 16 October, and again on 10 December until the end of January. While on loan at the club, Dickie was utilised in many different positions in the defence; right back, centre back and on the right side of a back three. During Cheltenham Town's 3–1 victory over
Chelmsford City in the
FA Trophy on 12 December, Dickie scored a
hat-trick. Dickie returned to Reading on January to recover from an injury, before rejoining Cheltenham Town for their promotion push on 23 March, helping them secure the
title against
Halifax Town on 16 April. On 25 August 2016. Dickie re-joined Cheltenham Town on loan until 2 January 2017.
Lincoln City (loan) On 1 August 2017, Dickie joined
Lincoln City on loan until January 2018. Dickie made his debut 5 days later in a 2–2 draw against
Wycombe Wanderers. During his short time at the club, Dickie kept captain
Luke Waterfall out of the team and he claimed that his partnership with
Sean Raggett helped him improved his game.
Oxford United On 4 January 2018, Dickie joined
Oxford United on a two-and-a-half-year contract for an undisclosed fee from Reading. He made his debut on 13 February in a 3–1 League One defeat at
Rotherham United, and scored his first goal for the club against
Peterborough United in a League One home fixture on 17 March 2018. During the
2018–19 campaign, Dickie established himself as a key player making 49 appearances and made a fundamental partnership with
Curtis Nelson which lead to an upturn in form. After spending large parts of the season in the relegation zone, Dickie helped them achieve a 12th-placed finish. On 31 July 2019, Dickie signed a new two-year contract keeping him at the club until the summer of 2021. During the
2019–20 season, Dickie proved crucial to Oxford's performances in
League One after Curtis Nelson joined Cardiff making Dickie first choice. On 25 January 2020, Dickie partnered with
Elliot Moore to produce a clean sheet against
Premier League side
Newcastle in the
FA Cup fourth round in what was his 100th appearance for the club, On 18 February 2020, Dickie became the captain for the first time in a 5–0 win over
AFC Wimbledon due to an injury to regular captain
John Mousinho. It was announced that he would remain captain for the rest of the season. Dickie helped them reach to the League One
play-off final where they lost 2–1 to
Wycombe Wanderers. Dickie was voted the Supporters' Player of the Year for
2019–20.
Queens Park Rangers Dickie signed for
Championship club
Queens Park Rangers on 1 September 2020, joining on a four-year deal for an undisclosed fee. Former QPR and Oxford player
Jamie Mackie urged Dickie to sign for QPR and snub
Premier League offers claiming it would be better for his long-term development. He scored his first goal for QPR in a 2–1 loss to
Bristol City on 1 December 2020. On 6 March 2021, Dickie scored his second goal for the club against the same opponents as QPR beat Bristol City 2–0 away from home. In his first season at the club, Dickie won Supporters' Player of the Year, Players' Player of the Year and Goal of the Season for his long-ranged goal at
Middlesbrough on the 17 April 2021.
Bristol City On 5 June 2023, Dickie signed for Championship side
Bristol City for an undisclosed seven figure fee, signing a three-year contract with the option for a further year. He was voted as the club's Player of the Month for October 2023 and February 2024. On 15 October 2025, the club announced Dickie had signed a contract extension until 2028. ==International career==