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On 13 April 2020, it was revealed that he had been given the all-clear from the pancreatic cancer that he had been suffering from for 17 months.

In October 2019, Vialli was appointed as new delegation chief of the Italy national football team under head coach and personal friend Roberto Mancini (a former teammate and striking partner of his at Sampdoria), a position unfilled since Luigi Riva's retirement in 2013; on that occasion, Vialli confirmed he was still suffering from pancreatic cancer.

In November 2018, Vialli revealed that he had successfully overcome a year-long battle with cancer.

Vialli also co-founded sports investment platform Tifosy, alongside ex-Morgan Stanley and Goldman Sachs investment banker Fausto Zanetton, with the aim of allowing anybody to invest in professional sports. Co-founder and CEO Fausto Zanetton explained that, “whilst there is an incredible passion and willingness to invest in sports, there is currently no way to do so for the average fan or investor...You no longer need to be a billionaire to invest in professional sports clubs.". At Web Summit 2016 Vialli discussed his latest venture with Tifosy.

The following season Chelsea won the European Super Cup by beating Real Madrid 1–0, and finished third in the Premier League, just four points behind champions Manchester United in what was Chelsea's highest league finish since 1970, and perhaps their most serious bid to win a league title since their first title triumph in 1955.

The following season saw Chelsea make their debut in the UEFA Champions League, where they reached the quarter-final. After a 3–1 quarterfinal first leg victory over FC Barcelona, they were eventually knocked out on aggregate following a 5–1 return leg loss at Camp Nou after extra time. Despite a fifth-place finish in the Premier League, the campaign ended on a high note when Vialli guided Chelsea to a win over Aston Villa in the 2000 FA Cup final.

In 2006, Vialli released The Italian Job: A Journey to the Heart of Two Great Footballing Cultures, co-written with his close friend and reputable football journalist, Gabriele Marcotti. Written over a period of two and a half years from November 2003 until early 2006, the book discusses the differences between English and Italian football. He also attributes his tendency to play as a wide attacker to playing on a field that was short and wide as a young boy. Vialli is donating the proceeds of the book to the "Fondazione Vialli e Mauro per la ricerca e lo sport", which is a charitable foundation he founded together with former player Massimo Mauro in order to raise funds for research into cancer and amyotrophic lateral sclerosis (ALS).

Son to a self-made millionaire, Vialli was brought up with his 4 siblings in the 60-room Castello di Belgioioso in Cremona. Vialli has been married to Cathryn White-Cooper since 26 August 2003 and has two daughters, Olivia and Sofia. He is a keen golfer and has played at the Dunhill links championship pro-am event.

Vialli then took up an offer to manage First Division club Watford in 2001–02. Despite making wholesale and expensive changes to the playing and coaching staff, the Hertfordshire side finished an unimpressive 14th and Vialli was sacked after one year. Following this, he was drawn into a lengthy dispute with the club over the payment of the remainder of his contract.

The 2000–01 season started brightly, with Chelsea beating Manchester United to win the Charity Shield, Vialli's fifth official trophy with the club in less than three years, making him the club's most successful manager at the time. Vialli was sacked five games into the season after an indifferent start and having fallen out with several players, including Gianfranco Zola, Didier Deschamps and Dan Petrescu.

Since the late 2000s Vialli works as a TV football commentator for Sky Italia. In 2007, he was linked with a move to the managers position at Queens Park Rangers, following the club takeover by Flavio Briatore and Bernie Ecclestone and the dismissal of John Gregory as manager, but ultimately declined any interest in the job. During Euro 2012, he appeared as pundit for the BBC's coverage of the tournament.

Vialli retired from professional football at the end of the 1998–99 season to focus on his position as Chelsea's manager. He made his last professional appearance in Chelsea's final match of the 1998–99 Premier League, scoring the winning goal against Derby County at Stamford Bridge.

Gullit was sacked as Chelsea manager in February 1998 and 33-year-old Vialli was appointed player-manager, becoming the first Italian to manage in the Premier League. Chelsea were already in the semi-finals of the League Cup and the quarter-finals of the European Cup Winners' Cup, and went on to win both competitions under Vialli, as well as finishing fourth in the Premier League. In beating VfB Stuttgart at the Cup Winners' Cup final on 13 May 1998, 33 years and 308 days old Vialli became the youngest manager to ever win a UEFA competition. The record stood for thirteen years until 18 May 2011 when FC Porto's André Villas-Boas won the Europa League at the age of 33 years and 213 days.

During the 1997–98 season, Vialli scored four goals in a league win over Barnsley and a hat-trick against Norwegian side Tromsø in the Cup Winners' Cup, but still could not cement his place in the side under Gullit. However, following Gullit's dismissal in early 1998, Vialli assumed the role of a player-manager, winning the Cup Winners' Cup in 1998, and the League Cup. He followed these victories up by a 1–0 victory over UEFA Champions League winners Real Madrid in the 1998 UEFA Super Cup.

Vialli joined Chelsea in the summer of 1996 on a free transfer as part of manager Ruud Gullit's rebuilding of the side. The team won the FA Cup in Vialli's first season, with the Italian scoring two goals in a 4–2 comeback over Liverpool in the fourth round. However, a feud with Gullit saw him regularly left out of the starting line-up; in the final itself he was limited to a five-minute appearance as a late substitute.

Vialli moved to Juventus shortly after the 1992 European Cup final loss for a world record fee of £12.5million. Vialli won the UEFA Cup in his first season with Juventus playing alongside players such as Roberto Baggio, Pierluigi Casiraghi, Paolo Di Canio, and Andreas Möller, among other players, under manager Giovanni Trapattoni. Following the arrival of manager Marcello Lippi, Vialli underwent an intense fitness and muscle strengthening training regime in order to lose weight, and gain speed, agility, physical strength, and stamina. Vialli refound his goalscoring form throughout the season, and through his leadership and decisive performances, he helped Juventus win the Scudetto (his second overall) and the Italian Cup in 1995, scoring 16 goals during the season; the club also narrowly missed out on a treble after suffering a defeat in the 1995 UEFA Cup Final to Parma, despite Vialli scoring a spectacular second leg goal. He ended his time in Turin by captaining the side to a Supercoppa Italiana victory and a Champions League final win over defending champions Ajax Amsterdam in 1996, playing alongside Del Piero and Fabrizio Ravanelli. During his four seasons with the club he totaled 102 appearances, scoring 38 goals.

Vialli returned to lead Italy's attack during the qualifying games to the Euro 1992 Championship under Vicini, scoring in Italy's 3–1 win over Hungary and 2–0 win over Cyprus. However, Italy missed out on qualifying after finishing second behind the Soviet Union in Group 3.

Vialli made his last appearance for the Azzurri in December 1992, due to his strained relationship with coach Arrigo Sacchi bringing his international career to a premature end, despite his club success during the 1990s. It is rumored that Vialli played a prank on Sacchi, which was the reason for his dropping from the national team.

At Sampdoria he formed a prolific strike partnership with teammate and childhood friend Roberto Mancini, earning the nickname The Goal Twins ("I Gemelli del Gol", in Italian). With Vialli at his best, Sampdoria had the most successful era in its history. They won their first ever Serie A championship in the 1990–91 season, in which Vialli was league top scorer with 19 goals – celebrating many of his goals with a backflip, including one against Inter – one UEFA Cup Winners' Cup (1990) – where he scored both goals in the 2–0 win over Anderlecht in the final (once again finishing the tournament as top-scorer), and three Italian Cups (in 1985, 1988 and 1989), also setting a record of 13 goals in a single edition of the Coppa Italia during his time at the club. They also won a Supercoppa Italiana, and reached the final of the UEFA Supercup, and the European Cup final in 1992, losing to Johan Cruyff's Barcelona "Dream Team" of Spain 1–0.

With the 1990 FIFA World Cup being held on home soil, Vialli named part of the squad and he was expected to make a huge impact for the hosts. However, after failing to score in the first match against Austria, despite setting up the winning goal via a cross, Vialli missed a penalty against the United States in the next match, hitting the lower near post with keeper Tony Meola diving the other way. He was subsequently dropped from the team in favour of Roberto Baggio and Salvatore Schillaci, who had scored the winning goal against Austria after appearing as a substitute. Vialli returned to the team for the semi-final against Argentina and played a role in Italy's opening goal after his shot on goal was blocked by Argentina keeper Goycochea and the rebound fell to Schillaci. He was substituted in the second half as Italy were eliminated on penalties, eventually finishing the tournament in third place. Because Italy assigned jersey numbers alphabetically to players for the World Cup (beginning with defenders, then midfielders, and finally attackers) Vialli wore the number 21 during the World Cup. Overall, he finished the tournament with 2 assists, which were both provided for the golden boot winner Schilacci.

Vialli scored his first goal for Italy in a UEFA Euro 1988 qualifier against Malta in 1986. He was included in Italy's squad for the finals of the Euro 1988 competition and scored the winning goal against Spain in the group stage. Although Italy were knocked out by the Soviet Union in the semi-final after losing 0–2, Vialli was named in UEFA's team of the tournament.

At international level, Vialli represented Italy in two FIFA World Cups, in 1986 and 1990 on home soil. He also took part at UEFA Euro 1988, helping his nation to a semi-final finish, and was elected to the team of the tournament. During his twenty years long career as a professional footballer he scored 259 goals at club level, 16 goals with the national team, and 11 goals with the Italy national under-21 football team, for a total of 286 goals in more than 500 appearances, making him the tenth-highest scoring Italian player in all competitions.

In 1985, Vialli made his debut for the Italy senior team in a friendly match against Poland. He was included in Italy's squad for the 1986 FIFA World Cup held in Mexico, appearing with an all-shaved head as a substitute in all four of Italy's matches.

Vialli was a member of Italy's under 21 team for both the 1984 and 1986 UEFA European Under-21 Football Championships where the Azzurrini finished third and second respectively. Overall Vialli represented the Italy U21 team 20 times, scoring 11 goals. He was also the top scorer in the 1986 Under-21 European Championship, with 4 goals, where Italy lost the final to Spain on penalties.

Vialli started his club career at Cremonese in 1980 in his native Italy where he made 105 league appearances scoring 23 goals. His performances impressed Sampdoria who signed him in 1984. During which time he scored 85 league goals, won 3 Italian cups, the Serie A and the European Cup Winners Cup. Vialli transferred to Juventus for a World record £12.5 million in 1992. During this time he won the Italian Cup, the Serie A, Italian Supercup, UEFA Champions League and the UEFA Cup. In 1996 Vialli joined Chelsea and became Chelsea player manager the following season. In England he won the FA Cup, League Cup, UEFA Cup Winners Cup and UEFA Super Cup. He is one of nine footballers to have won the three main European club competitions, and the only forward to have done so; he is also the only player in European footballing history to have both winner's and runner's up medals in all three main European club competitions, including two winners medals for the UEFA Cup Winners' Cup.

Vialli's career started in 1980 when he signed for local club Cremonese in Serie C1, winning promotion to Serie B. After scoring ten goals for the club in the 1983–84 Serie B season, he was transferred to Sampdoria.

Gianluca Vialli (Italian pronunciation: [dʒanˈluːka viˈalli] ; born 9 July 1964) is an Italian former football manager and player who played as a striker. Since retiring, he has gone into management, punditry and worked previously as a commentator for Sky Sport Italia.