Motherwell (first spell) McFadden was raised in
Springburn,
Glasgow and attended
Turnbull High School in
Bishopbriggs. His parents operate a
fish and chips takeaway in
Glasgow city centre. He joined the
Motherwell youth system at a young age, making his first-team debut when he was 17 years old. McFadden came to greater prominence during the
2002–03 Scottish Premier League SPL season, scoring 19 goals from 34 starts and winning the
Young Player of the Year Award. In this season Motherwell finished bottom of the SPL and should have been relegated but were given a reprieve due to
First Division champions
Falkirk not meeting stadium criteria. McFadden received some criticism for his lack of discipline, picking up fifteen yellow cards and one red during the campaign. McFadden's final game for Motherwell that season saw him score a hat-trick in a 6–2 defeat of
Livingston at
Fir Park. McFadden scored his debut goal for Everton during their 5–2 defeat at
Tottenham Hotspur on 1 January 2005, and ended the season with seven goals. After nearly three months on the sidelines, he made a scoring return to action for Everton as a second-half substitute versus
Charlton Athletic on 15 April 2007. In October 2007, McFadden scored a critical equalising goal in Everton's victory over
Metalist Kharkiv in the
UEFA Cup. He dedicated his goal against
Middlesbrough on 2 January 2008 to the recently deceased
Phil O'Donnell, by pointing to his black armband and then to the sky in tribute to the former Motherwell captain.
Birmingham City On 18 January 2008, McFadden joined
Birmingham City on a three-and-a-half-year deal, with an option for additional two years, for an initial fee of £5 million, potentially rising to £6m depending on appearances. McFadden's first goal arrived in his fourth game for the club, a
penalty kick versus
West Ham United at
Upton Park, after he had been fouled by
Lucas Neill. In his next match, at home to
Arsenal, he scored from a 20-yard free kick before adding the equalising goal from the penalty spot in the last minute of
stoppage time. McFadden scored Birmingham's first goal of the
2009–10 Premier League season, a 92nd-minute penalty, to give the club a 1–0 home win against
Portsmouth. He returned to training in March 2011, but suffered a setback which meant he could not play in the 2010–11 season. Following their relegation from the Premier League, Birmingham chose not to take up a two-year option on his contract but attempted to negotiate amended terms. No agreement was reached, and McFadden left Birmingham after his contract expired on 30 June 2011.
Everton (second spell) After continuing to train with Birmingham over the summer to regain fitness while out of contract, McFadden had a successful trial with
Wolverhampton Wanderers in September, but was unable to agree contract terms. In mid-October he was reported to be in talks with
Celtic, but on 17 October, McFadden signed for Everton until the end of the
2011–12 season. McFadden played in a
reserve team match the following day, his first appearance since a knee injury 13 months earlier Again out of contract, McFadden trained with Motherwell during the 2012–13 pre-season, Contract speculation followed when Motherwell manager
Stuart McCall made an approach to sign McFadden. However, the approach to sign McFadden was unsuccessful as no agreement could be met.
Sunderland In September 2012, McFadden undertook a trial with Sunderland. On 26 October, he joined Sunderland on a three-month contract that ended in January 2013. McFadden's debut was on 15 December 2012, in a 3–1 defeat to
Manchester United at
Old Trafford and his home debut was on 12 January 2013 in a 3–0 victory versus West Ham United. McFadden made his first start on his return in a 2–1 win over Celtic. McFadden then scored the late equaliser in a 2–2 draw versus
St Mirren on 6 April 2013 and then on 5 May 2013, scored a brace despite losing 4–3 versus
Inverness Caledonian Thistle. his future still remained uncertain. At the start of pre-season training for the 2013–14 season, McFadden returned to the club and travelled with them to their training camp in Spain. In a 4–2 defeat versus Newcastle United in a friendly match, McFadden scored a penalty with an audacious chip down the centre of the goal, known as a
Panenka. After the match, reports suggested that McFadden would remain at Motherwell on a one-year deal. On 19 July 2013, it was confirmed that McFadden had signed a new contract in a decision that he described as "straightforward". At the start of the
2013–14 season, McFadden started as a traditional right winger but soon afterwards his form and fitness slumped, having scored only once versus Livingston in the last sixteen of the Scottish League Cup. McFadden then suffered a back injury but returned soon after to score his first league goal of the season in a 5–1 win over
Partick Thistle on 29 December 2013 and followed this up his second league goal in the next match, in a 4–0 victory over
St Johnstone. and he went on to score and provide three assists, on 1 March 2014 as Motherwell defeated
Hearts. McFadden's fourth goal arrived on 22 March 2014 in a 2–1 victory over
Ross County. even though he had expressed his desire to sign a new contract two months previously.
St Johnstone On 1 October 2014, McFadden signed for St Johnstone until the end of the 2014–15 season and had his debut on 4 October 2014 in a 2–1 defeat versus St Mirren. As of September 2015, McFadden was training with Motherwell. Two months later, he entered negotiations to be the marquee player of
Indian Super League club
Kerala Blasters, after the departure of
Carlos Marchena.
Motherwell (third spell) On 18 December 2015, McFadden signed a short-term deal until the end of January 2016. That arrangement expired at the end of January, with McFadden expecting to move on to the USA. On 13 February, McFadden signed a new deal to stay to the end of the season. On 19 March, he was ruled out for the remainder of the
2015–16 season, after suffering a broken ankle in training. On 26 July 2016, Motherwell announced that McFadden had been appointed as the club's assistant-manager, whilst also continuing as a player until the summer of 2017. Nearly seventeen years after making his Motherwell debut, and nearly sixteen after scoring his first league goal, McFadden came on as a second-half substitute in Motherwell's final game of the 2016–17 season versus Inverness Caledonian Thistle and scored his final Motherwell goal in his final appearance. The match ended in a 3–2 win for the
Scottish Highlands club. On 13 November 2019, it was announced that McFadden was to be inducted into the Motherwell Hall of Fame.
Queen of the South On 8 September 2017, McFadden signed for
Dumfries club
Queen of the South on a short-term contract. McFadden departed Queens in January 2018, after 15 appearances for the club. ==International career==