Madden signed league forms with Bohemians on 8 July 2008, and scored several times for the Bohemians "A" Team on their path to the Grand Final of the A League in that year. He made his Bohemians first team debut as a substitute in their 2–0 win over Cobh Ramblers on 8 November 2008. Prior to the start of the 2009 season, Madden joined Shelbourne on loan on 10 February 2009. Bohemians manager Pat Fenlon sent the young striker out on loan hoping for Madden to gain first team experience. Madden made an immediate impression for Shelbourne by scoring in his first competitive appearance for Shels in their opening First Division match against Wexford Youths at Tolka Park on 6 March 2009. He also scored against his own employers for Shelbourne during an EA Sports Cup 2nd round tie at Dalymount Park on 4 May 2009. Madden's loan spell at Shelbourne concluded on 29 June 2009 and he returned to Bohemians. During his loan spell at Shelbourne, Madden made 16 league and cup appearances and scored 8 goals. On 29 September 2009, Madden scored his first goal for Bohs in a 1–0 victory over Derry City in the Brandywell which led to Bohs returning to the top of the league. In the 2010 season, Madden scored 9 goals in 5 matches, and he was voted the Soccer Writers Association of Ireland Player of the Month for June. Madden signed for English League One side Carlisle United on 31 January 2011, for an undisclosed fee signing a two-and-a-half-year contract with the Cumbrian club. On 4 October 2012, Madden joined League One club Yeovil Town on an initial one-month loan deal with a view to extend to gain some much needed pitch time after not featuring in Carlisle's starting league squad this season. He had scored 1 goal in 3 substitute appearances for the Cumbrians this campaign. On 6 October 2012, he made his debut for Yeovil and scored a two goals in a 3–1 home victory against Colchester United. After going on a run of five goals in five games, he extended his loan until 2013. On 1 January 2013, Madden scored a brace in the final match of his loan spell against Leyton Orient ending with nine goals from sixteen games for Yeovil. Following the game it was announced Madden had signed permanently for Yeovil Town for an undisclosed fee on a two-and-a-half-year deal. Madden then went on to score 4 goals in his first two games as a permanent Yeovil Town player in the month of January. By mid February he was already League One top scorer, with 18 goals, despite only starting playing in October. In an interview with the BBC after this run of form he was described by his manager Gary Johnson as "the bargain of the season". Madden's contribution of 6 goals to Yeovil's perfect January of 3 out of 3 wins didn't go unrecognised as he won the League One Player of the Month award. Madden scored in the 2013 League One play-off Final as Yeovil beat Brentford 2–1 to earn promotion to the Championshipfor the first time in the club's history. Madden ended the season with the League One golden boot with 23 goals, plus his 2013 League One play-off Final goal to make it 24 in all competitions. On 26 November 2013, with Madden having failed to score since Yeovil's promotion to the Championship, he was placed on the transfer list by the club. On 10 January 2014, Madden signed for Football League Two side Scunthorpe United for an undisclosed fee, believed to be £300,000, signing a -year contract. Madden's first game for Scunthorpe came on 11 January 2014 in a 0–2 away win over Mansfield Town. He scored his first goal for the club in a 5–1 win over Portsmouth on 22 February 2014. Madden helped the club gain promotion to League One at the end of the 2013–14 season, scoring 5 goals in the process. For the following two seasons, Madden was the club's most prolific goalscorer, netting 16 goals in all competitions during 2014–15, and 23 goals in all competitions during 2015–16. Madden suffered a significant downturn of form during Scunthorpe's play-off push in the 2016–17 season, despite featuring in the majority of the Iron's games. This downturn in form continued into the next season, with Madden scoring only 2 league goals during the very early stages of the 2017–18 season. Madden failed to score in any of his last 16 league appearances for the Iron. Despite his downturn in form, Madden scored 60 goals across all competitions during his time with the Iron, placing him as the club's 10th most prolific goalscorer of all time. On 2 January 2018, Madden signed for fellow League One side Fleetwood Town for an undisclosed fee, believed to be £150,000, signing a -year contract. He scored his 100th goal in English football in Fleetwood Town's FA Cup against Guiseley. In May 2019 he signed a new three-year contract with the club.
