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Madine re-signed for Blackpool on 16 January 2020 on a one-and-a-half-year deal.

On 7 January 2019, he joined Championship side Sheffield United on loan for the remainder of the 2018–19 season, which saw United promoted to the Premier League. In January 2020, Madine left Cardiff after his contract was cancelled by mutual consent.

On 31 January 2018, Madine joined Cardiff City for an undisclosed fee. His debut came three days later in a 4–1 win over Leeds United.

On 8 June, Madine signed a two-year deal with Bolton Wanderers . On 26 September, he scored his first goal for Bolton in a 2–2 draw with Brighton & Hove Albion. On 31 May 2017 the club confirmed that Madine had signed a new two-year contract, keeping him at the club until 2019.

Madine joined Blackpool on loan until the end of the 2014–15 season on 10 February 2015.

On 27 March 2014, Madine re-joined his former club Carlisle United on loan until the end of the 2013–14 season.

Madine re-joined Coventry City on a one-month loan on 30 October 2014. He scored in the club's 1–0 victory over Colchester United on 22 November after scoring his first goal back in the Football League Trophy tie against Plymouth Argyle F.C. at the Ricoh Arena. He was named the club's Player of the Month by Coventry Telegraph in December, after scoring again in a 2–0 victory over Port Vale at Vale Park on 13 December.

In November 2010 Madine was found guilty of causing actual bodily harm after attacking a man in a pub and sentenced to community service involving 250 hours of unpaid work. He was also ordered to pay £1,500 compensation to his victim and £1,800 in costs. In October 2013 he was jailed for 18 months after being found guilty of causing actual bodily harm and grievous bodily harm in two separate attacks. Madine was released from jail on 20 February 2014 after serving five months of his sentence.

On 15 January 2011, Madine signed for Sheffield Wednesday, signing a four and a half year contract. He made his debut on 22 January in a 4–0 away loss to Leyton Orient. He scored on his second appearance 3 days later, in a 2–2 draw against Yeovil Town at Hillsborough. He scored again the following game in a 5–3 defeat to Peterborough at London Road. His next goal came in a 4–0 win against Tranmere, and his final goal of the season came in a 2–0 win against Preston North End. He finished the season with 18 goals in all competitions for both Carlisle and Sheffield Wednesday. He scored his first goal of the 2011–12 season in a 2–1 win against Notts County on 20 August 2011. On 27 August he scored a brace as Sheffield Wednesday beat Scunthorpe United 3–2. On 10 September he scored a brace in a 3–1 win against MK Dons, and went on a 4-game goal-scoring run, scoring goals against Stevenage and Yeovil, and a brace against Exeter. He scored his 10th goal of the season in a 3–1 win against Chesterfield. He scored in the following game, this time in a 2–2 draw against city rivals Sheffield United. The game is known as the Steel City derby, and after being two goals down, Wednesday scored two goals in the last 10 minutes including Madine's 85th-minute header to make the score 2–2. This was his first Sheffield derby. He was named Football League Young Player of the Month for September, after scoring 10 goals in 12 games. On 25 October he was sent off for the first time in his career, in a 3–2 loss at former club Carlisle. He broke his toe during a 2–1 win against Tranmere on 19 November and was out for six weeks. He bounced back from his injury by scoring in his second game back during a 2–2 draw against Hartlepool. On 6 March 2012, he scored in a 4–1 win against Bury. Later that month he scored in back to back games in a 2–1 win against Notts County and an injury time equaliser in 2–2 draw against Walsall. On 31 March he scored two goals as Sheffield Wednesday beat Preston 2–0 at home. He scored his first league goal of the 2012–13 season on 9 November, in a 3–1 defeat away to Middlesbrough.

He progressed through the youth ranks of Carlisle, making his debut at the age of 17 on 3 March 2008, in a 1–0 away win against Nottingham Forest, coming on as a substitute for Danny Graham in the 92nd minute. He went on to make 12 appearances that season, before signing a new three-year contract in June 2008. His first appearances of the following season came in the League Cup, a 1–0 win away to League Two side Shrewsbury Town and a 4–0 defeat to Championship side Queens Park Rangers. He scored his first goal for the club in a 4–1 win in the league against Yeovil Town on 30 August 2008. His next goal came on 7 October in the Football League Trophy, making the score 2–2 after Rochdale had taken a 2-goal lead. The game went to penalties and Madine scored his however Carlisle lost the shoot-out 4–3. He scored on his FA Cup debut as Carlisle drew 1–1 to Grays Athletic at Brunton Park on 8 November. He played in the replay which Carlisle won 2–0, however Carlisle were eliminated in the next round by Crewe. On 20 March 2009, Madine signed on a month-long loan for League Two team Rochdale. He made his debut the next day, setting up Adam le Fondre to score a last-minute winner as Rochdale beat Wycombe 1–0. He made a further two appearances before returning to Carlisle. He scored his first goal of the following season in a 2–0 League Cup win over Championship side Bristol City, helping Carlisle into the third round of the League Cup for the first time since 1976. He made regular appearances before joining Championship side Coventry City on a three-month loan on 19 October 2009. He made his debut on 24 October in a 0–0 draw against West Brom at the Ricoh Arena. He made 9 appearances before returning to Carlisle on 20 January 2010. He made 4 appearances including a Football League Trophy Northern Area Final win on penalties against Leeds United, scoring his penalty in the shoot-out. He then joined League Two side Chesterfield on a month-long loan deal on 12 February. He made 4 appearances before returning to Carlisle. He played and scored in the Football League Trophy Final on 28 March 2010 at Wembley, scoring a consolation goal as Carlisle lost the game 4–1 to Southampton. He began to find form and scored 4 goals in the last six matches of the season, with the goals coming against Brighton, Oldham, Southampton, and in a 2–0 win against league winners Norwich on the final day of the season. He scored on the opening day of the 2010–11 season, in a 2–0 home win against Brentford. His next goal came in a 4–1 win against MK Dons on 21 August. On 28 September, he scored a hat-trick in a 4–0 away win against rivals Hartlepool United. After goals against Notts County and Charlton, he scored 4 goals in a 6–0 FA Cup win against Tipton Town. In November, he scored in back-to-back games against Rochdale and Tamworth. He played his final game for Carlisle on 8 January 2011 in a 1–0 away defeat to Torquay United in the FA Cup. He finished his Carlisle career with 83 appearances and 22 goals.

Madine began his career with Carlisle United, where he made his first team debut in 2007. He was sent out on loan in 2009, first with Rochdale and then Coventry City before joining Chesterfield in 2010 on loan. He signed a permanent contract with Sheffield Wednesday in January 2011 for an undisclosed fee.

Madine was born in Gateshead, Tyne and Wear. He attended local secondary school Lord Lawson of Beamish Comprehensive School from 2001–2006. He was originally on the books of Middlesbrough, however he was released and joined Carlisle. Newcastle United players Alan Shearer and Chris Waddle were his heroes growing up.

Gary Lee Madine (born 24 August 1990) is an English professional footballer who plays as a striker for Blackpool.