Dickinson started his career at Stoke City, and had loan spells at Víkingur (Iceland) and Blackpool before helping the "Potters" to win promotion into the Premier League in 2007–08. He then dropped out of the first team picture, and spent time on loan at Leeds United, Barnsley, and Portsmouth. He was sold to Watford for a £250,000 fee in July 2011 and was a first team regular in the 2011–12 campaign. However, he fell out of favour the following season and was loaned out to Portsmouth and Coventry City before being allowed to join Port Vale on a free transfer in July 2013. He spent three years with Port Vale, and also served as club captain, before he moved on to Notts County in June 2016.
Dickinson spent his early youth at the Derby County academy, before he joined Stoke City's academy in 2002. He made his senior debut on 11 December 2004, replacing Carl Asaba in the last moments of a 1–0 victory over Coventry City at the Britannia Stadium.
His next first team involvement came on 1 April 2006, when he played the full ninety minutes of a 1–1 draw with Sheffield United. Two days later he signed a professional contract with the club. He played four further Championship games in what remained of the 2005–06 season. His chance to shine at first team level came after manager Johan Boskamp decided to blood Stoke's young players.
Dickinson spent summer 2006 on loan at Icelandic club Víkingur, along with teammate Keith Thomas, and played two Úrvalsdeild games.
He played four games for Stoke at the beginning of the 2006–07 season, before he was allowed to join League One side Blackpool on a one-month-long loan on 20 October. Manager Simon Grayson later extended the loan for a further month, as Dickinson continued to cover for injured left-backs Danny Coid and Paul Tierney. He played a total of ten games during his time at Bloomfield Road. After returning to Stoke, Dickinson put in a series of impressive performances at left-back. His commitment and ability led to him becoming a firm favourite with the club's supporters and earned him a contract extension.
Dickinson played 27 times for Stoke during the 2007–08 season as Tony Pulis led the "Potters" to promotion into the Premier League.
He played in the first three opening Premier League games for Stoke before he lost his first team to Danny Higginbotham. On 15 January 2009, Dickinson joined Leeds United on a one-month loan, having been signed by Simon Grayson for the second time in his career. He made his first appearance for the club two days later at Brighton, where Leeds won 2–0. In total he made seven League One starts at Elland Road and was recalled to Stoke at the end of the loan period, despite Leeds wishing to extend the deal. In total, he played five top-flight games in the 2008–09 campaign.
On 23 September 2009, Dickinson joined Championship side Barnsley on loan for three months, along with fellow teammate Ryan Shotton. He scored his first goal in the Football League on 21 November, with a 93rd minute free kick against Cardiff City that proved to be the only goal of the game at Oakwell. He remained with Mark Robins's "Tykes" for the rest of the 2009–10 season, putting in 29 appearances. A knee injury picked up in mid-March ended his season prematurely.
Dickinson joined Championship side Portsmouth on loan for the whole of the 2010–11 season. He went on to play 39 games for Steve Cotterill's "Pompey", though started just 23 league games.
In July 2011, Dickinson signed for Sean Dyche's Watford on a three-year contract. The fee for the deal was undisclosed, though was thought to be in the region of £250,000. Dickinson's work rate and robust style of defending earned him comparisons with former Watford fans' favourite Paul Robinson at the start of his Watford career. He scored his first goal for the "Hornets" on 27 September against fellow relegation strugglers Millwall, in a 2–1 win at Vicarage Road. He also scored a long-range strike against Bristol City in a 2–2 draw on 29 November. He ended the 2011–12 campaign with 41 appearances to his name.
On 22 October 2012, Dickinson re-joined former club Portsmouth on an initial monthlong loan. Manager Michael Appleton was replaced by Guy Whittingham during this spell, and Whittingham decided not to extend Dickinson's loan. On 12 February 2013, Dickinson joined Coventry City on a 28-day loan, in a move that reunited him with former Barnsley boss Mark Robins. He started six League One games for both Portsmouth and Coventry. On 24 July 2013, Dickinson had his contract at Watford cancelled by mutual consent, after being deemed surplus to requirements by manager Gianfranco Zola.
Dickinson joined Port Vale in July 2013, signing a one-year contract. Manager Micky Adams stated that: "Carl has performed at a higher level than League One and that experience will be invaluable for us, especially as he can perform at centre-back as well as left-back." He was well received by Vale supporters despite previously being a popular player at local rivals Stoke. He opened the 2013–14 season in a centre-back partnership with Chris Robertson, and said he "enjoyed the challenge" and that "if I can make centre-half my shirt, happy days." He managed to start every game until picking up a suspension in mid-October. His performances made him a strong contender for the club's Player of the Year award and made him a popular player with supporters. At the end of the season he signed a new two-year contract.
He was appointed as club captain in August 2014, taking the armband from the departed Doug Loft. He scored his first goal for the "Valiants" and only his fourth career goal in a 3–1 victory at Doncaster Rovers on 16 August. However, he was dropped from the starting line-up two months later after admitting "I haven't been good enough for the standards I set myself every day". After returning to the first team he stated that a talk with manager Rob Page helped him to calm down as he had put "a bit too much pressure" on himself after taking over the captaincy. He remained in poor form however, but said the criticism from the fans did not affect him after providing the assist for Tom Pope in the win against nearby rivals Walsall on 14 February.
He was an ever-present for the first 26 games of the 2015–16 season before being sent off for an off-the-ball incident in a 2–1 defeat at Rochdale on 28 November; earlier in the game he also gave away a penalty though opposition manager Keith Hill admitted Dickinson had made an "excellent challenge... I think the referee has got that wrong". Whilst serving his suspension he defended his teammate's from booing, stating that negative fans who booed should "shut up and get behind the team". He was offered a new contract in the summer, though the offer included a "considerable pay cut". He announced his departure from the club in June 2016.
Dickinson signed a two-year contract with EFL League Two side Notts County in June 2016. He and the club endured a difficult 2016–17 campaign, which Dickinson said was the most "mentally challenging" of his career after the "Magpies" faced a change of ownership, manager and an unexpected relegation battle. He had expected to help lead a promotion charge under manager John Sheridan, but ended the season at Meadow Lane fighting on-loan Arsenal defender Marc Bola for the left-back spot under new boss Kevin Nolan.
Dickinson is a vocal player.As of 9 May 2017.
with Stoke City
Football League Championship runner-up: 2007–08