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Shortly after leaving Dunfermline, Shiels signed an 18-month pre-contract with League of Ireland Premier Division side Derry City, where he would once again play under his father. It was announced on 15 January 2019 that Shiels had left the club.

On 30 January 2019, it was announced that Shiels had joined Coleraine on an 18-month contract. However, the contract was terminated via mutual agreement in August 2019.

In February 2017, Shiels signed for FC Edmonton of the North American Soccer League. He was released on 10 July 2017.

After his release from the NASL, Shiels returned to Scotland with Championship club Dunfermline Athletic. In November 2017, two players from Falkirk, Dunfermline's local rivals, were charged with 'excessive misconduct' for taunting Shiels over his visual impairment during a Scottish Challenge Cup fixture between the sides, following an incident during the match in which Shiels had been sent off. Both players were given lengthy suspensions. Shiels left Dunfermline at the end of his contract, having played 25 times for the side.

On 10 June 2016, Shiels left Rangers after his contract came to an end. He had made 43 appearances for Rangers in his final season with the club, as they won promotion to the Scottish Premiership.

On 25 August 2016, Shiels signed for Dundalk in the League of Ireland Premier Division citing the "lure of European football" as one of the things that attracted him to the club. The move reunited him with his former teammate from his youth career at Arsenal, Stephen O'Donnell. Shiels made his debut the following day in a 1-0 win over Wexford Youths, coming on as a substitute in the 73rd minute. He scored his first goal for the club in a 5-0 FAI Cup Third Round win against Crumlin United on 30 August. He left the club at the end of the 2016 season.

On the opening game of the 2013–14 season, Shiels scored as Rangers won 4–1 against Brechin City. Shiels sustained another knee injury in October 2013. Two months after his return, Shiels scored a brace, in a 2–0 win over East Fife on 11 January 2014. Shiel's lack of playing time led to transfer speculation with moves linked to Partick Thistle and returning to Hibernian after the rumoured cost-cutting that is due to take place at the club; manager Ally McCoist refuted this. On 8 February 2014, Shiels scored a hat-trick in the Scottish Cup, as Rangers won 4–0 against Dunfermline Athletic.

Shiels signed for Rangers on 31 July 2012. Kilmarnock's chairman Michael Johnson believed Rangers had undermined Kilmarnock to get Shiels. Shiels vowed to help the club win a trophy that season and claimed he had turned down other clubs around Europe and could have played in the Champions League; instead, preferring to join Rangers.

He scored a goal, as well as, setting up two goals in his first appearance, in a Scottish League Cup tie against East Fife on 7 August. A week after he sustained an injury during a match which ruled him out for weeks, On 2 September 2012, Shiels scored his first league goal, as well as setting up a goal, in a 5–1 win over Elgin City. After scoring two goals in three games, Shiels scored against the Scottish Premier League side Motherwell, in a Scottish League Cup tie. Then, in the Scottish Cup, Shiels scored twice and earns a hat-trick assist, as Rangers thrashed Alloa Athletic 7–0 on 3 November 2012. During the 2012–13 season he missed five months of the season due to a medial knee ligament injury.

Shiels signed a six-month loan deal with Kilmarnock, managed by his father Kenny Shiels, in July 2011. Shiels made his first appearance for Kilmarnock on 30 July 2011, in a goalless draw against Motherwell at Rugby Park, coming on as a 74th-minute substitute. Shiels scored his first goal for Kilmarnock in a 2–1 away defeat to Inverness CT. He scored a penalty in a 1–0 win over Hearts, after Marius Zaliukas fouled Paul Heffernan. Shiels signed for Kilmarnock on a permanent basis in January 2012. Shiels scored the only goal of the Scottish League Cup semi-final against Ayrshire derby rivals Ayr United on 28 January. He also scored the winning goal in a game against Rangers at Ibrox on 18 February, in Rangers' first game after entering administration. On 18 March, he played in the 2012 Scottish League Cup Final, which Kilmarnock won after beating Celtic 1–0. Shiels was shortlisted for the SPFA Players' Player of the Year award, along with Jon Daly, Steven Davis and Charlie Mulgrew. Shiels rejected the offer of a new contract with Kilmarnock and left the club at the end of the season.

Shiels, whose contract with Hibernian was due to expire in the summer of 2009, signed for Doncaster Rovers on 2 February 2009. He was transferred for a fee of around £50,000. He made his Rovers debut on 21 February 2009, coming on as a second-half substitute in a 3–1 defeat at Swansea City. His first goal for the club came in the last home match of the 2008–09 season, when he scored the first goal in a 2–0 victory over Crystal Palace.

Shiels scored six goals in 42 games during the 2009–10 season. However, during the 2010–11 season Shiels lost his place in the Doncaster starting line-up. He was loaned to Kilmarnock in July 2011 and his contract was mutually terminated in January 2012.

Shiels returned to action after his eye operation later in 2006. He re-established himself in Hibs' first team squad in the 2006–07 season, scoring in the team's first two league matches. He scored his first hat-trick for Hibs on 12 January 2008 in a 3–0 win over Inverness Caledonian Thistle in the Scottish Cup, but Shiels struggled to establish himself as a Hibs first-team regular throughout his time at Easter Road.

Shiels won his first Northern Ireland cap against Portugal in November 2005. He was recalled to the squad for the match against Scotland in August 2008 after an absence of 18 months. Shiels appeared as a second-half substitute in the goalless draw at Hampden Park. Northern Ireland manager Michael O'Neill said in February 2012 that Shiels could still have an international future. O'Neill selected Shiels during the 2012–13 season despite him playing in the Scottish Third Division. Shiels scored his first international goal on 12 September, in a 1–1 draw against Luxembourg.

Shiels started his professional career at Arsenal, but made no first team appearances for the club before signing for Hibernian in 2004. In early 2006, Shiels had an operation to remove his right eye, which had been blind since a domestic accident when he was eight years old. The damaged eye was causing headaches and it was agreed that surgery was the best solution. In November 2008, St Mirren apologised to Shiels after one of their supporters verbally abused him regarding his disability during a match at Love Street. Hearts also criticised their supporters after they taunted Shiels about his disability during an Edinburgh derby match.

Dean Andrew Shiels (born 1 February 1985) is a British professional footballer, who plays as an attacking midfielder, and is currently a free agent. Shiels has previously played for Hibernian, Doncaster Rovers, Kilmarnock, Rangers, Dundalk, FC Edmonton and Dunfermline Athletic. He has also played in 14 full international matches for Northern Ireland. His father is Kenny Shiels, who was his manager at Kilmarnock.