Di Canio was born in Rome, in the district of Quarticciolo, a working-class area populated mainly by A.S. Roma fans. However, Di Canio was drawn to their local rivals S.S. Lazio. As a young boy, he was addicted to cola and similar drinks and called Pallocca, a slang term meaning lard-ball. He was fat, and knock-kneed, and needed to wear orthopedic shoes – "But I never hid. My response was to exercise; to try to become the kind of person I am."
He signed for Lazio in 1985 and remained there until 1990. Lazio won promotion to Serie A in 1988, having narrowly escaped relegation to Serie C1 the year before. He finally made his first-team debut in October 1988 and went on to play 30 games during the 1988–89 season.
Di Canio scored the winner in the first Rome derby of the season, a goal which contributed to Lazio's survival in Serie A that season and earning him hero status. In 1990 he was sold to another of Italy's biggest clubs, Juventus; although he won the UEFA Cup with the Turin side in 1993, he struggled to gain playing time during his tenure with the club, due to the presence of other forwards and creative midfielders in the team, such as Roberto Baggio, Salvatore Schillaci, Pierluigi Casiraghi, Fabrizio Ravanelli, Gianluca Vialli, and Andreas Möller. He left Juventus after an "animated exchange" with then manager Giovanni Trapattoni and spent the 1993–94 season with Napoli. Two seasons followed at A.C. Milan, where, despite winning the Serie A title in 1996, he once again struggled to gain playing time due to heavy competition from his team-mates, culminating in another row, this time with Fabio Capello.
In July 1996 he joined Celtic in Scotland, and enjoyed a successful season in Glasgow, scoring 15 goals in 37 appearances[9] and winning the SPFA Player of the Year award. His time in Glasgow was dogged by controversy though; sent-off during a 2–2 draw against Hearts in November 1996 and heavily involved in an acrimonious league match against Rangers in March 1997 where he behaved aggressively towards Ian Ferguson and gestured in the direction of Rangers’ bench as he was led from the field by team-mates. The Italian was called to the referee’s room after the teams had returned to the dressing room and was shown another yellow card in addition to the one he had received earlier in the game. Di Canio then demanded a large wage rise at the end of the season, but this was rebuffed by Celtic. He then refused to join the Celtic squad in the Netherlands for their pre-season training during July 1997.
On 6 August 1997, Di Canio moved to the English Premiership as he joined Sheffield Wednesday in a transfer deal valued at around £4.2 million. Whilst in Sheffield, Di Canio was the club's leading goal scorer for the 1997–98 season with 14 goals and he became a favourite of the fans.
In September 1998, Di Canio pushed referee Paul Alcock to the ground after being sent off while playing for Sheffield Wednesday against Arsenal at Hillsborough, which resulted in an extended ban of 11 matches and him being fined £10,000.
In January 1999, Di Canio signed for West Ham United for £1.5 million. He had not played football since his ban following his push on Paul Alcock. West Ham manager, Harry Redknapp on signing Di Canio admitted he was taking a chance but said of the player "He can do things with the ball that people can only dream of". Di Canio said of his ban, "I made a mistake and I'm sorry, West Ham have given me a big chance and I'm very happy" He scored his first goal for West Ham on 27 February 1999 in his fourth game. Playing against Blackburn Rovers, Di Canio made the first goal in a 2–0 win, for Ian Pearce in the 27th minute and scored the second in the 31st minute. He helped them to achieve a high league position (5th) and qualify for the UEFA Cup through the Intertoto Cup.
- Paul Alcok's BAFTA winning fall
He was also the OPTA player of the season 1998–99. He scored the BBC Goal of the Season in March 2000 with a flying volley against Wimbledon, which is still considered among the best goals in Premiership history and was named as the Premiership's goal of the decade in a December 2009 Sky Sports News viewers' poll, scoring 30% of votes. In this season he was also voted Hammer of the Year by the club's fans.
In December 2000, late in a game against Everton and with both sides vying for the winning goal, Di Canio shunned a goal-scoring opportunity and stopped play, grabbing the ball from a cross inside the box, as the Everton goalkeeper Paul Gerrard was laying injured on the ground after he twisted his knee attempting a clearance on the edge of the box. The Goodison Park crowd reacted with a standing ovation. FIFA officially lauded Di Canio's gesture, describing it as "a special act of good sportsmanship," and awarded him next year the FIFA Fair Play Award.
- Do the Barthez
Sir Alex Ferguson tried to sign him for Manchester United halfway through the 2001–02 season, but his attempts were unsuccessful and Di Canio remained in East London for another season and a half.
In 2003, with the Hammers struggling at the bottom of the league, Di Canio had a very public row with manager Glenn Roeder and was dropped from the first team. However, he returned at the end of the season (after Roeder, stricken by a brain tumour, was replaced by Trevor Brooking) and scored a winner against Chelsea in the penultimate game of the season, a game that boosted West Ham's chances of staying in the Premiership. However, they were relegated on the final day of the season after a 2–2 draw away to Birmingham City, where Di Canio scored an 89th-minute equaliser. He was released on a free transfer and signed with Charlton Athletic for the start of 2003–04.
In his only season at The Valley, Di Canio helped the Charlton Athletic secure 7th position, its highest league finish since the 1980s. However, he only scored four league goals for the Addicks, all of them from the penalty spot (one of them scored from a rebound). These penalty kicks included an audacious 'Panenka' style penalty kick against Arsenal. Di Canio however continued to be a provider of goals as well, notably in October 2003 when he came on as second-half substitute with Charlton trailing 0–1 away at Portsmouth. He provided most of the spark for Charlton's much-improved second-half display, and after Jonathan Fortune had equalised for Charlton, it was from Di Canio's corner kick in the last minute that Shaun Bartlett headed home the winning goal.
Even though he had already signed an extension to his Charlton contract, in August 2004 he returned to his home team of Lazio taking a massive paycut in order to return to the economically stretched Roman team. Lazio fans were happy to have a Rome-bred Lazio supporter in the team again, something missing since the departure of Alessandro Nesta in 2002. He scored in the Rome derby, just as he had in 1989, leading the team to a 3–1 victory over A.S. Roma in January (6 January 2005). However the negative publicity that Di Canio generated for Lazio, including his intimate relationship with club's ultras and their increased influence thanks to his presence in the team, coupled with problems with some teammates and coaches, exasperated club president and majority shareholder, Claudio Lotito, with whom he already had a difficult relationship. As a result, Di Canio's contract was not renewed in the summer of 2006. During several of his games for Lazio, Di Canio made a fascist salute to their right-wing fans. He subsequently signed with Cisco Roma of Serie C2 on a free transfer. In his first season with Cisco Roma, his team failed promotion to playoffs, despite a runners-up position in the regular season. He subsequently agreed to stay with Cisco for another season, in a second attempt to win promotion to Serie C1 with the Roman side.
On 10 March 2008, Di Canio announced his retirement from football, ending his 23-year playing career before the end of the season due to physical issues. It was his intention to begin coaching lessons at Coverciano to gain a coaching position. In an interview he revealed that his dream would be to manage former club West Ham, and applied for the position after the resignation of Alan Curbishley in September 2008. Di Canio played in Tony Carr's testimonial game at Upton Park on 5 May 2010, which featured a West Ham team against West Ham Academy old boys. He played for both sides during the match. The West Ham team won 5–1. In July 2010, in honour of Di Canio, West Ham announced the opening of the Paolo Di Canio Lounge, within the West Stand, at their Upton Park ground, which was formally launched by the unveiling of a plaque by Di Canio himself, on 11 September 2010.
On 20 May 2011, Di Canio was appointed manager of Swindon Town, following the club's relegation to League Two. Di Canio began his career as a manager with an emphatic 3–0 win over Crewe Alexandra on 6 August 2011. On 30 August 2011, Di Canio was involved in a pitch-side altercation with Swindon striker Leon Clarke after their defeat in the League Cup to Southampton. In January 2012, Swindon caused a FA Cup shock by defeating Premier League club Wigan Athletic 2–1. Di Canio stated that he believed his players deserved to have their names put on the stadium and dedicated the victory to his father, who died late in 2011. He was sent to the stands later in the month in a league game against Macclesfield Town for vociferously venting his frustration at his side not being awarded a free-kick. Swindon won the match 1–0 and with over half the season gone, his team were fighting for promotion to League One.
Under Di Canio, Swindon reached the 2012 Football League Trophy Final, where they were defeated 2–0 by Chesterfield.
- As always swamped by fans for autographs
On 21 April 2012, Swindon were promoted to the League One after Crawley Town's 1–1 draw with Dagenham & Redbridge and Torquay United's 2–0 loss to AFC Wimbledon, despite Di Canio's side having lost 3–1 to Gillingham on the same day. He dedicated the promotion to his parents, his mother having died shortly after his father in April of that year. One week later, Swindon won the Football League Two thanks to an emphatic 5–0 victory over Port Vale.Swindon finished the season on 93 points.
Although in the 2012-13 season, Swindon were knocked out of the FA Cup and the Football League Trophy in their first game against opposition from lower leagues, they did have a solid run in the League Cup in which they won against three teams from higher leagues. They beat Brighton & Hove Albion 3–0, won against Stoke City 3–4 after extra time, and beat Burnley 3–1 before narrowly missing out against Aston Villa 3–2 at home.
In January 2013, with Swindon under a transfer embargo and in financial difficulty, Di Canio offered to pay £30,000 of his own money to keep loan players John Bostock, Chris Martin, and Danny Hollands at the club.
On 18 January 2013, ahead of Swindon's Saturday clash with Shrewsbury Town, Di Canio worked into the night alongside approximately 200 volunteers to clear a snow-covered pitch at the County Ground, thus allowing the game to go ahead. He showed his appreciation by ordering everyone pizza. Swindon won the match 2–0, which Di Canio publicly deemed a present to the volunteers.
In January 2013, the Swindon Town chairman announced that due to financial difficulties, no money would be made available for future signings. Di Canio offered to pay £30,000 of his own money to keep loan players at the club. With the possibility of the club entering administration, a new buyer was found, subject to Football League approval, and without the knowledge of Di Canio, player Matt Ritchie was sold to Bournemouth. Further attempts to sign players by Di Canio were rejected by the Football League due to the club's financial situation with Di Canio "considering his future" at Swindon due to off-field financial problems. In February, Di Canio offered his resignation but said he would withdraw this if approval for the new owners, by the Football League, was received by 18 February. This did not happen and he resigned as manager of Swindon Town.
On 31 March 2013, Sunderland announced the appointment of Di Canio on a two-and-a-half-year contract, following the dismissal of Martin O'Neill the previous day. The appointment prompted the immediate resignation of club vice-chairman David Miliband due to Di Canio's "past political statements". The appointment of Di Canio also sparked opposition from the Durham Miners' Association, which decided to remove one of its mining banners from Sunderland's Stadium of Light, which is built on the former site of the Wearmouth Colliery, as a symbol of its anger over the appointment. The background to the opposition was past statements made by Di Canio supporting fascism.
Di Canio was tasked with keeping Sunderland in the Premier League, following a run of only three points from a possible 24. His first game as manager of Sunderland resulted in a 2–1 away defeat to Chelsea. Di Canio's second game in charge was the Tyne-Wear derby against Newcastle United at St James' Park on 14 April. Sunderland defeated their fierce rivals 3–0, their first away victory in the fixture in over a decade. Each goal sparked wild celebrations from Di Canio and the Sunderland bench. Di Canio then got his first win at the Stadium of Light against Everton.
Although the team did not win the next three matches, including drawing the final two home games and a heavy 6–1 defeat to Aston Villa, Sunderland secured their Premier League survival when Wigan Athletic were defeated at Arsenal and relegated, trailing then-17th placed Sunderland by four points with only one game to play.
For the 2013–14 season, Di Canio signed fourteen new players and sold experienced players such as Simon Mignolet, James McClean and Stéphane Sessègnon. After five league games, Sunderland had gained only a single point, from an away draw with Southampton. Di Canio was sacked on 22 September 2013, the day after the fifth game of the season, a 3–0 defeat to West Bromwich Albion, and only his thirteenth game in charge. Sunderland chief executive officer Margaret Byrne stated that Di Canio had been sacked after senior players had approached her and that his situation became untenable due to his "brutal and vitriolic" criticism of the squad. Di Canio denies this
