Dobbie began his career in 2002 at Rangers followed by other generally unremarkable spells at Hibernian and St Johnstone. Dobbie's career was revived by a loan spell at Dumbarton in 2006. Dobbie then scored 54 goals in 98 appearances for Queen of the South in his first spell at Palmerston Park. Dobbie played in the club's first ever appearance in the Scottish Cup Final in 2008.
Dobbie moved to Swansea City in 2009. Dobbie was loaned to Blackpool and won promotion to the Premier League, winning the 2010 play-offs. Dobbie returned to Swansea City and won promotion to the Premier League, winning the 2011 play-offs. Dobbie was again loaned to Blackpool in 2012 and played in a third successive play-off final, this time as a runner-up. In 2012 Dobbie signed for Brighton & Hove Albion, before joining Crystal Palace. Dobbie then helped the Selhurst Park club to win promotion in 2013 to the Premier League but on this occasion was not part of the play-off winning team.
Dobbie then had a third spell at Blackpool and played for Fleetwood Town and Bolton Wanderers, before returning to Scotland in August 2016 to sign for Queen of the South for a second spell.
Born in Glasgow, Dobbie started his career at Rangers, but failed to break into the first team despite being prolific in the reserve side. In 2002, he went on loan to Australian National Soccer League club Northern Spirit, scoring three goals in three league games in the 2002–03 season. He was transferred to Hibernian in 2003 after no first-team league appearances for Rangers.
Dobbie made his debut on 9 August 2003 as an 85th-minute substitute in a 2–1 win over Dundee United at Tannadice Park. After five substitute appearances, he made his full debut on 23 September, scoring a hat-trick in a 9–0 win over Montrose in the second round of the 2003–04 Scottish League Cup. His full league debut came four days later in a 1–2 defeat to Celtic at Easter Road, and he scored his first league goal on 7 December in a 1–3 defeat to Aberdeen at Pittodrie Stadium.
On 5 February 2004, in the semi-final of that season's Scottish League Cup at Hampden Park against his former club Rangers, Dobbie scored the equalising goal in the 79th minute. The game ended 1–1 after extra time and Hibs won 4–3 on penalties. Despite this, Dobbie failed to win a regular place in the Hibernian first team as Garry O'Connor and Derek Riordan were preferred. Dobbie was a 70th-minute substitute in the 2004 Scottish League Cup Final defeat by Livingston. Hibs lost 2–0 to goals by Derek Lilley and Jamie McAllister.
He made a total of 33 appearances, scoring six goals that season. On 3 July, he made his European debut in the second round of the 2004 UEFA Intertoto Cup, as a 76th-minute substitute, in a 1–1 draw with Lithuanian A Lyga side Vėtra at Easter Road. He then started the 2004–05 season with Hibernian, making seven League and three League Cup appearances.
A lack of opportunities at Hibs under the management of Tony Mowbray meant that Dobbie was sent on loan to Scottish First Division side St Johnstone on 26 January 2005. His debut came on 19 March, as a 57th-minute substitute in a 2–0 defeat to Ross County at McDiarmid Park and he scored his first goal in a 4–0 win over Partick Thistle at Firhill on 16 April. He made a total of eight appearances for the club that season, scoring two goals. The transfer to St Johnstone was made permanent in the summer of 2005, going on to make a total of 27 appearances scoring 4 goals in the 2005–06 season.
He struggled to hold down a regular place in the team, and the following season he was loaned out to Scottish Third Division Dumbarton, where he found some form, scoring ten goals in seventeen league games. He made his debut on 19 August 2006 in a 1–0 defeat to Queen's Park at Hampden Park. His first goal came in his second match for the club, a 3–1 defeat to Inverness Caledonian Thistle at the Caledonian Stadium in the second round of the Scottish League Cup. He made a total of 18 appearances on loan at Dumbarton, scoring 11 goals.
Dobbie's form at Dumbarton was noticed by Dumfries based Scottish First Division club Queen of the South who signed him from St Johnstone on 5 January 2007. He made his debut the following day in a 1–1 draw at Dundee in the third round of the 2006–07 Scottish Cup at Dens Park. In the replay, a 3–3 draw at Palmerston Park ten days later, Dobbie scored his first two goals for the club. Queen's went on to win the tie 4–2 on penalties After scoring another brace in a 4–3 home league win over Partick Thistle on 27 January, he scored again in the 2–0 fourth round victory over Cowdenbeath in the Scottish Cup. He then grabbed a third brace on 17 February in a 3–0 win over Airdrie United at the Excelsior Stadium. He then played in the quarter finals of the Scottish Cup as Queen's lost 2–1 to his former club Hibernian. He scored 13 goals in a total of 19 appearances that season.
With Gordon Chisholm appointed manager for the 2007–08 season, Dobbie and Queens embarked upon a club history making Scottish Cup run. He scored twice in the third round as Queen's beat Peterhead 5–0 at the Balmoor Stadium on 24 November 2007. He added another goal in the fourth round 4–0 home win over Linlithgow Rose on 12 January 2008. Queen's then beat Greenock Morton 2–0 in the fifth round on 2 February.
Dobbie's opening goal in a 2–0 home win in the quarter-final against Dundee on 8 March helped to take Queens to their first Scottish Cup semi final since 1950. The second goal was scored by Ryan McCann with a notably long range shot from 84 yards. Queens then progressed to their first ever Scottish Cup Final by beating Aberdeen 4–3 in the semi-final on 12 April. Dobbie started the semi-final at Hampden Park, but had to be substituted approaching half time due to injury. Despite second half goals by Steve Tosh and Jim Thomson, Queens' lost 2–3 to Rangers in the final on 24 May, with Dobbie being substituted in the 82nd minute. Dobbie was Queens' top scorer for the 2007–08 season with 20 goals in a total of 44 games as the club finished fourth in the First Division.
Dobbie played in Queens' 2008–09 UEFA Cup campaign in August 2008, in which they lost 2–4 over two legs to Danish Superliga side FC Nordsjælland in the second qualifying round. Despite being the most prolific goal scorer at Queens since Andy Thomson in the early 1990s, Chisholm elected to leave Dobbie out of the starting line up for both games, preferring Stewart Kean.
The 2008–09 season saw Dobbie score 23 goals in 32 league games, including four in one game, a 7–1 home win over Clyde. All four goals came in just 13 minutes in the second half of the game.
On 6 May 2009, Queen of the South announced Dobbie was moving to Wales to play for Championship side Swansea City. Dobbie said of the move "I'm sad to leave Queen of the South as I felt I'd struck up a good bond with the fans those past two and a half years. However, it's an offer I just couldn't refuse! I'd like to say a big thank-you to the manager, the players, coaching staff at Palmerston and I'll never forget my time there. If I'm not playing any week don't be surprised to see me in the stand watching Queens in action. Good luck to you all." Dobbie was the first player to transfer between the two clubs since Tommy Lang in 1938.
Swansea City confirmed on 7 May 2009 that they had agreed personal terms with Dobbie who would be moving to the South Wales club, subject to a medical at the Liberty Stadium. He passed the medical on 22 May, signing a three-year deal with the club on a free transfer. His first two goals for Swansea came in a 3–0 win at home to Brighton & Hove Albion in the first round of the 2009–10 League Cup on 11 August 2009. His third goal came in the next round of the League Cup, a 1–2 defeat at home to Scunthorpe United on 25 August. This gave Dobbie three goals in six games for Swansea at this point. However he lost his team place due to injury and played only two more games for Swansea in 2009.
On 1 February 2010, Dobbie signed for fellow Championship side Blackpool on loan until the end of the season, with a view to a permanent move.
Two days later he scored on his debut, in a 3–2 defeat to West Bromwich Albion at Bloomfield Road. On 6 February, in his first full appearance, he found the net again in the 89th minute of a 2–1 home defeat to Leicester City. Dobbie scored a crucial goal in a play-off semi final against Nottingham Forest that earned Blackpool a place in the Wembley final. Dobbie made a second-half substitute appearance in the 3–2 play off final win against Cardiff City.
After his loan spell with Blackpool, Dobbie returned to Swansea City. After Paulo Sousa left the club to manage Leicester City, new Swansea manager Brendan Rodgers gave Dobbie more chances in the first team. With Craig Beattie and Gorka Pintado out injured, leaving only Shefki Kuqi to compete with for the lone striker role in the team, Dobbie was heavily relied on to score goals.
Dobbie scored in a 4–0 home win against Preston North End on 14 August 2010, his first goal in 12 months for Swansea, which he dedicated to Besian Idrizaj. The following month he put Swansea 1–0 up against Leeds United in the 13th minute, but they went on to lose 2–1. After Shefki Kuqi was loaned to Derby County, Dobbie was the only fit and available striker at the club while Rodgers looked elsewhere for a loan signing. West Ham striker Frank Nouble arrived at the club on a three-month loan deal as competition for Dobbie. Dobbie was dropped to the bench but later came on and scored to make it 2–0 to the Swans. On 28 September 2010 his next goal came at Watford, which gave Swansea a 3–2 win.
From October to January, Dobbie was only used as a substitute and failed to score any goals as he was replaced by Middlesbrough loan signing Marvin Emnes and a returning Craig Beattie. It became more difficult for Dobbie to get a chances in the team when Jermaine Easter joined for a month on loan from Milton Keynes. On 28 December 2010 at home to Barnsley, Dobbie was given a rare start, alongside Jermaine Easter. Easter scored the only goal of the game, while Dobbie impressed in what seemed to be an attacking midfield role.
After Luke Moore was signed from West Brom, Dobbie continued to be kept on the bench. On 22 February 2011, away at Coventry City, Dobbie came from the bench to score the winning goal in a 1–0 win. It was his first goal in 5 months. On 8 March 2011 he opened the scoring with an early goal at home to Watford, with the final score being 1–1. He scored three goals in the last two games of the season, which helped Swansea finish third in the table.
During the first leg of the semi-final play-off match away at Nottingham Forest, left back Neil Taylor was sent off after only a minute into the game. In order to bring on a defender to reorganise the team, Rodgers substituted Dobbie moments later. Dobbie scored the second goal in the home leg against Forest, which helped secured Swansea a place in the final with a 3–1 aggregate victory.
Dobbie then played in the 2011 Football League Championship play-off Final at Wembley, a second successive successful appearance in the play off final. A 4–2 victory against Reading, Dobbie scored his side's third goal and also set up one for Scott Sinclair. Swansea City made history by becoming the first Welsh team to play in the division since its formation in 1992.
After Swansea were promoted to the Premier League, Dobbie made his Premier League debut for Swansea City in a 4–0 loss against Manchester City. Dobbie went on to make 7 appearance in the Premier League but as yet is to score in the Premier League. Dobbie suffered an ankle injury. It seems that Dobbie twisted his left ankle under a challenge from Kyle Naughton. His injury kept him out of action for a week until he returned to action against Manchester United. After making just 8 appearance in the Premier League, Dobbie found himself in a pecking order behind striker Danny Graham, Leroy Lita, Luke Moore and new signing Rory Donnelly. Finding his first team appearances limited, manager Brendan Rodgers allowed Dobbie to leave on loan after his former club Blackpool made an enquiry on him. Birmingham City made an enquiry to sign him but lack of finances meant they could only bring Dobbie in on loan with a view to a permanent deal. However, neither Birmingham City or Blackpool signed him on loan before the close of the transfer window on 31 January 2012.
After failing to move to a new club in the January transfer window, Rodgers was quoted as saying he understands Stephen Dobbie's frustration at a lack of playing time, but says he will not be allowing Dobbie to head out on loan as he has been restricted to a supporting role this season and Swansea may need the cover if an injury occurs.
On 22 March 2012, it was confirmed that Dobbie finally sealed a loan move, returning to Blackpool on loan until the rest of the season. Dobbie played in the 2012 Football League Championship play-off Final at Wembley on 19 May 2012, a third successive appearance in the play off final.
On 31 August 2012, Dobbie transferred to Brighton & Hove Albion for an undisclosed fee, signing a three-year contract.
In January 2013, Dobbie joined Crystal Palace on an initial loan deal lasting until the end of the season. He completed a permanent transfer on 1 July 2013, signing a two-year contract. On 16 July 2014, he scored four goals in a 13–1 pre-season friendly win against GAK Graz. On 22 May 2015, it was announced that Dobbie would not be offered a new contract by Palace at the end of the 2014–15 season.
On 17 September 2013, Dobbie returned to Blackpool on a three-month loan. He made a substitute appearance for Blackpool that evening in the away fixture against Millwall. He made his first full appearance for the club against the same side he made his original debut against, Leicester City. That time he suffered a 1–2 home defeat, despite scoring an 89th-minute goal. Three years later he played 66 minutes in a 2–2 draw, substituted in the second half for Ángel Martínez. He scored two goals in back-to-back games against Brighton & Hove Albion and Wigan Athletic in April 2014 to help move Blackpool out of the relegation zone.
On 7 August 2014, Dobbie joined League One side Fleetwood Town on loan until the end of the season, which was when his Palace contract expired and he left the club.
On 5 August 2015, Dobbie joined Championship side Bolton Wanderers on a one-year deal, and made his debut from the bench on 11 August in a Capital One Cup game against Burton Albion, which Bolton lost 1–0.
Dobbie scored his first goal for Bolton Wanderers on 22 August when he scored just minutes after coming onto the pitch to snatch a late equaliser against Nottingham Forest, with the game finishing 1–1. At the end of the 2015–16 season, the club confirmed that he would be leaving when his contract expired at the end of June.
On 3 August 2016 Dobbie signed for Queen of the South once more. After initially signing up until the end of the 2016–17 season, Dobbie then extended his contract on 26 August 2016 up until May 2018. Dobbie was appointed the club's vice-captain on 7 January 2017 and scored 26 goals (19 league & 7 cup) in his first season back in Dumfries.
Dobbie is currently the 9th highest goalscorer in the club's history with 90 goals.As of 17 September 2017
When Dobbie moved from Swansea to Blackpool in February 2010, his wife Susanne was nine months pregnant and already overdue. When he made his debut for the Seasiders on 3 February, she was five days overdue. He said: "My wife is in a hotel on the prom. I've got a house organised, which we are about to move into. It has been a bit rushed. It was a case of a quick pack in Swansea, so the baby will be born in England now." A baby boy was born the following weekend.Hibernian
2004 Scottish League Cup Final runner up
Queen of the South
2008 Scottish Cup Final runner up
2010 Football League Championship play-off Final winner
2012 Football League Championship play-off Final runner up
2011 Football League Championship play-off Final winner
2012-13 Football League Championship promotion