A technically gifted creative playmaker and set piece specialist, renowned for his curling free-kicks, dribbling skills, and goalscoring, Baggio is widely regarded as one of the greatest players of all time.

[33] During the end of his final season at Vicenza, Baggio shattered both the anterior cruciate ligament (ACL) and the meniscus of his right knee while playing against Rimini on 5 May 1985, while attempting a slide tackle.

Although several team doctors feared he would not play again, Fiorentina retained their faith in him, agreeing to commit to the transfer as well as fund the required surgery, one of many reasons for Baggio's attachment to the club.

He had a dominant season, winning the only European club trophy of his career after helping Juventus to the UEFA Cup final, in which he scored twice and assisted another goal over both legs, defeating Borussia Dortmund 6–1 on aggregate.

[96][97] After strong pressure from AC Milan chairman Silvio Berlusconi and manager Fabio Capello, Baggio was sold to the Milanese club for £6.8 million, amidst several protests from Juventus fans.

Baggio refound his form with the club and had a dominant season, scoring a personal best of 22 goals in Serie A, as well as providing 9 assists, leading Bologna to an eighth-place finish, allowing them to qualify for the UEFA Intertoto Cup.

[132] After injuries, disappointing results, and several managerial changes throughout the season, including Luigi Simoni, Mircea Lucescu, and Roy Hodgson, Baggio struggled to gain playing time,[36][52][133] and was used out of position as a winger, often as a substitute.

[148] Baggio ultimately transferred to Serie A newcomers Brescia under head coach Carlo Mazzone, aiming to save them from relegation; he remained in Italy in order to have a greater opportunity of being called up for the 2002 World Cup.

[163] Trapattoni also expressed concern about bringing Baggio to the World Cup due to the presence of Francesco Totti and Alessandro Del Piero in his role, believing that this could create a rivalry between the players.

[168] Baggio played his last career match on 16 May 2004 on the final matchday of the season at the San Siro against Milan, which ended in a 4–2 loss to the Serie A champions; during the game, he set-up Matuzalém's second goal.

[172] Baggio totalled 27 goals in 56 caps for his national team at senior level, making him Italy's fourth-highest all-time goalscorer, tied with Del Piero, who managed the tally in 91 appearances.

[4] His first senior International call-up was given to him by manager Azeglio Vicini, and he made his first appearance for Italy on 16 November 1988 at age 21 in a 1–0 friendly victory over the Netherlands, assisting Gianluca Vialli's match-winning goal.

Although Baggio was the regularly designated penalty taker for his national team, he stepped aside to allow Schillaci to score and capture the Golden Shoe, a gesture which was praised by the Italian media.

[205] The Italians finished third in their group, drawing much criticism from the press, and only advancing from the first round as the fourth-best third-placed team; Juventus president Gianni Agnelli famously called Baggio un coniglio bagnato ("a wet rabbit"), referring to his despondent demeanour, hoping the jab would spur him on to score.

[209][210] Baggio gave a man of the match performance in the semi-finals; he scored two more goals to beat Bulgaria 2–1 at Giants Stadium, leading Italy to the World Cup final for the first time in 12 years.

"[228] In 2017, Emmet Gates instead described Baggio's run-up to the 1994 World Cup final with Italy as "the greatest show of individual excellence since another equally majestic number ten [Maradona] dominated the 1986 tournament.

"[229] When summarising Baggio's 1994 World Cup in 2018, Ed Dove of ESPN FC stated that "'[t]he Divine Ponytail' had arguably been the outstanding player of the tournament, bailing Italy out on numerous occasions, but his inspirational touch deserted him when it mattered most.

[242] In Italy's 3–0 second group match win over Cameroon, Baggio assisted Luigi Di Biagio's opening goal with a cross following a corner; however, he was replaced by Del Piero during the second half after sustaining a minor injury.

[251] Baggio was initially a regular squad member under Dino Zoff, appearing as a substitute in two UEFA Euro 2000 qualifying matches, and in a 2–0 win against Wales in 1998, setting up a goal for Vieri;[252][253] and in a 1–1 draw against Belarus in 1999.

[254][255] Baggio made a starting appearance in a 0–0 friendly draw against Norway in 1999, creating several chances, helping to set-up a goal which was ruled offside, and hitting the post from a free-kick.

Zoff centred his squad around younger offensive players, such as Francesco Totti, Alessandro Del Piero, Stefano Fiore, Marco Delvecchio, Filippo Inzaghi and Vincenzo Montella.

[110][111][288] During the lead-up to the 1994 World Cup, he was also initially employed by Italy's manager Arrigo Sacchi as a centre-forward, in a role known in Italian football jargon as centravanti di manovra (which literally translates to "manoeuvring centre-forward"), which was a precursor to the modern false-nine role; in this position, Baggio was expected to link-up with other players and create chances for them, in addition to creating space with his movement by dropping deep into midfield, and allowing the team's wingers to cut inside and make attacking runs into the centre.

[310] Not particularly imposing physically, or in the air, due to his diminutive stature and slender physique,[6][290][311][312][313] he was known however for his pace and acceleration over short distances, which, along with his movement, positioning, anticipation, technical ability, quick feet, low centre of gravity, and resulting agility,[6][314][315][316][317] allowed him to lose his markers when making offensive runs into the area, both on and off the ball.

[271][314][316][318][319] Regarded as one of the greatest dribblers ever,[320][321][322][323][324][325] and as one of the most technically accomplished players of all time,[nb 6] Baggio possessed an excellent first touch,[273][280][327][331] and was renowned for his skilful dribbling, ball control and balance, as well as his spatial awareness, speed of thought and execution, reactions, close control at speed, and ability to beat opponents with flair, tricks, body feints, or sudden changes of pace or direction, both in one-on-one situations, or during individual dribbling runs.

[26] During his time at Juventus, the club's former chairman, Gianni Agnelli, referred to Baggio as an "artist",[349] comparing his elegance to the painter Raffaello, while he described the emerging talent Alessandro Del Piero as Pinturicchio.

"[381][385][386][387] Known to be an introvert in the media, due to his quiet private life and reluctance to give interviews, some in the sport, including Gianni Rivera, argued that Baggio lacked leadership qualities on the pitch.

His personality is thought to have limited him from being more successful, in particular with larger clubs, with some pundits instead arguing that he excelled more with smaller teams; others instead believed that he had a difficult character due to his disagreements with several of his managers throughout his career,[nb 9] although he was generally regarded as a "correct" and co-operative player by officials,[389][390] and as a classy and well-behaved footballer in the media.

[395][397][410][411] In 2004, Sacchi praised Baggio for his strength of character, which he believed even surpassed his talent, as it allowed him to overcome his injuries and physical struggles, and ultimately "win [his] personal battles against bad luck.

[416] In 2004, he was named by Pelé in the FIFA 100 list of the world's greatest living players,[22] and was voted 24th in the online UEFA Golden Jubilee Poll, celebrating the best European footballers of the past 50 years.

[427] In 2020, Jack Gallagher of 90min.com placed Baggio at number nine in his list of "The 50 Greatest Footballers of All Time",[428] while Sky Sports ranked him as the fifth-best player ever never to have won the Champions League or European Cup.