Raith & Sunderland

Beginning his career in Kirkcaldy with Raith Rovers, Shields scored in his first full start for the side in a match against Airdrieonians.^[1] After a successful start for The Rovers, Shields earned a move to Sunderland in December 2002, in a deal thought to be worth up to £100,000.^[2] Despite spending three years at the Stadium of Light, Shields never made a first-team appearance and was loaned to Scarborough scoring nine goals and then to Doncaster Rovers^[3] during his time in England. In January 2003, Shields returned to Raith on a free transfer,^[4] two years after leaving.

Brechin, Cowdenbeath & Gretna

Released after only spending a few months on his return as club went into administration Stark's Park,^[5] Shields joined Brechin City at the start of the 2003–04 season, only to move on loan closer to his home town Cowdenbeath.^[6] Cowden made the move permanent in early 2004, tying Shields to a two-and-a-half-year contract.^[7]

A year later, Cowdenbeath chairman Gordon McDougall said it would take an "exceptional offer" to sell Shields after interest from Gretna and Hearts,^[8] and it was Gretna's offer that saw Shields move to the Scottish Borders club in January 2005,^[9] where he made only three substitute appearances in what was the remainder of Gretna's title-winning season. He took part in the side's historic Scottish Cup run, playing in the Scottish cup Semi-final at Hampden park against Dundee.^[10]

Shields was loaned to Scottish First Division side Stranraer in the first few weeks of the 2005–06 season.^[11] On his return to Raydale Park, Shields played nine matches of Gretna's second successive title win, missing out on a winner's medal by one match. Shields was loaned out again at the start of the following season, this time to Stirling Albion,^[12] scoring nine goals in eighteen games, and although he played one match for Gretna on his return, it was to be his last before a January 2007 move to Ross County.^[13]

Ross County, East Fife & Raith

Shields spent two and half years in Dingwall winning the Scottish Second Division, scoring fourteen goals in thirty-six appearances. In September 2008, Shields made East Fife his eleventh club when he joined on loan for the rest of the year,^[14] failing to score in ten appearances for the Methil side. On 19 February 2010 after being a free agent he re-signed for Raith Rovers.^[15]

Malta

Shields signed for Hamrun Spartans in the Maltese Premier League in August 2010,^[16] spending two seasons with the side and scoring eighteen goals in twenty-eight games. Shields then signed for Xewkija Tigers in the Gozo First Division.^[17] In his first season with the club Shields scored eighteen goals, finishing as the side top scorer.^[18] His second season with The Tigers ended in a similar fashion to the first, with Shields again scoring eighteen goals in eighteen matches. In his final season with Xewkija, Shields helped the club win their seventh league title, scoring in a match against Kerċem Ajax.^[19]

Return to Scotland

After five years in Malta, Shields returned to Scotland signing for Scottish League One side Brechin City for a second time.^[20] Shields lasted only six months in his homeland, leaving the club in January 2016 to return to Malta for personal reasons,^[21] making his final appearance in a league match against Stenhousemuir which was abandoned after 45 minutes.^[22] Shields made 9 appearances for the city, scoring 2 goals.