In May 2009 it was announced he was moving to Derby County on a one-year deal, with the move set to be completed in July. He made his Derby debut as an 80th-minute substitute against Peterborough United on 8 August 2009. The following game of the 2009–10football season, Pringle started his first game for Derby in the League Cup 2–1 loss to League Two side Rotherham United. Pringle signed an extension to his Derby deal to take him through to the end of the 2010–11 season on 11 December 2009. Pringle was captain of the Derby County reserves side that won the 2009–10 Central League Central Section title and was also named the club's Young Player of the Season for the campaign. He was handed his first League start in the final game of the 2009–10 season against Cardiff City in a 2–0 win and earned the supporter's Man of the Match award. In February 2011, Pringle's contract was extended until summer 2012.
In March 2011, Pringle joined then League Two outfit Torquay United on a months loan. Pringle spent just 19 days of the loan at Torquay, playing five games, but returned to Derby after expressing a desire to fight for a place in the Derby first team rather than remain at Plainmoor. Upon his return to Derby, despite having had his contract extended at the end of the 2010–11 campaign, Pringle was told he was free to find another club.
Rotherham United
On 3 June 2011, it was revealed he had agreed personal terms with Rotherham United. The transfer was confirmed later that day, with Pringle joining The Millers on a free transfer, signing a two-year contract. He made his first team debut for Rotherham at home to Oxford United on 6 August 2011, and scored his first goal for the club in a 2–1 win over Crewe Alexandra on 16 August. He had made 9 appearances for Rotherham up until mid-October but following his substitute appearance versus Bristol Rovers he had not played again for them as of mid-February. However, he was an unused sub in Rotherham's game against Burton Albion on 18 February. Pringle's form, contributed greatly to the clubs' automatic promotion to League One at the end of the 2012–13 season. On 18 January 2013, Pringle signed a new two-and-a-half-year contract with Rotherham. His goals and assists during the 2013–14 season helped Rotherham reach the League One playoff final. Pringle played in the final, and after a 2–2 draw, Rotherham earned promotion after beating Leyton Orient 4–3 on penalties to earn a second successive promotion. At the end of the 2013–14 season, Pringle was voted in the 2013–14 Football League One PFA Team of the Year. On 9 August 2014, Pringle started for Rotherham in their opening fixture of The Championship season in a 1–0 defeat against his former club Derby County. On 23 August 2014, Pringle scored his first goal in The Championship with a winner in Rotherham's 1–0 victory against Millwall. On 9 January 2015, Rotherham agreed a fee with Millwall F.C. for Pringle, however Pringle turned down the move to the club. On 27 January 2015, Pringle scored his second goal of The Championship season in a 4–2 victory against Bolton Wanderers where he was also named man of the match.
On 4 July 2016, Pringle signed for Preston North End on a three-year contract for an undisclosed fee. On 31 August 2018, Pringle joined Grimsby Town on a season-long loan, however, his loan was cut short, with Pringle joining League 2 rivals Tranmere Rovers on 22 January 2018 He was released by Preston at the end of the 2018–19 season.
In September 2019, Pringle joined Gillingham on a contract intended to run until the end of the season. He went on to make 11 appearances for the Kent side in all competitions, but was released at the conclusion of the 2019–20 season.
Honours
Ilkeston Town
Northern Premier League Premier Division play-offs: 2009
