Early career Born in
Necoclí, Cuadrado first form of football development wasn't until his mother suggested him the idea at the age of 12, joining Manchester F.C. Apartadó, a youth academy located in
Apartadó, Antioquia. Consequently, his notable performances allowed him to join the youth setup of
Deportivo Cali after impressing their scouts. Cuadrado later joined Atlético Uraba, where his preferred position was as a
forward. However, on the recommendation of club founder Nelson Gallego, Cuadrado took on a
midfielder role, usually as a
winger. Cuadrado's confidence and ability in the position also allowed him to play occasionally as a
full-back or wing-back. He later had a brief spell at
Colombian second division club
Rionegro, where he languished on the bench under coach Víctor González Scott, but his potential was later recognized by manager Juan José Peláez of
Independiente Medellín.
Independiente Medellín He was eventually signed by Medellin in 2008, allowing him to return to the
first division. That year, Cuadrado made his senior professional debut against
Boyacá Chicó, a match in which he would also score his first goal. Cuadrado remained in Medellin until 2009, before making the leap to European football.
Udinese On 2 July 2009, Cuadrado signed with
Serie A club
Udinese on a five-year deal for an undisclosed fee. He played his first match for Udinese in a 2–1 win against
Chievo as a right
wing back. Cuadrado, however, was not given many first-team minutes for the rest of the season, and he would be sent on
loan to fellow Serie A side
Lecce.
Lecce (loan) On 3 August 2011, it was officially confirmed that Cuadrado would join Lecce for the
2011–12 season. He scored his first goal for the club against
Cesena, the sole goal in a 1–0 victory. In spite of further impressive performances from Cuadrado, however, Lecce finished 18th and was
relegated to
Serie B. He would then return to Udinese. Around this time, he was watched by an unidentified English club who deemed that at 23 years he was too old to be signed by the club. He scored his first goal for the
Florence club in a 4–1 victory at home against
Cagliari. He finished the season with five goals and six assists, an integral part of a side that finished fourth in
Serie A. In June 2013,
La Viola purchased half of the
registration rights of Cuadrado for €5 million. He was booked after scoring the winning goal, and suspended for the final, which his team lost 1–3 to
Napoli on 3 May. On 16 June 2014, amid media speculation of a move to a larger club by the player, Fiorentina agreed a deal to purchase full ownership of Cuadrado's contract from Udinese, for an additional €12 million.
Chelsea on 7 February 2015On 2 February 2015,
Premier League club
Chelsea announced the signing of Cuadrado from Fiorentina on a four-and-a-half-year deal,
for a reported initial fee of £23.3 million, which could potentially rise to £26.8 million;
Mohamed Salah went the other way on loan. While in Fiorentina's financial filing of year 2014, in the management report (), Fiorentina declared the fee was €30 million. Five days after signing, Cuadrado made his Chelsea debut after replacing
Willian for the last ten minutes of a 2–1 win away against
Aston Villa. On 11 February, he made his first start in his first appearance at
Stamford Bridge, playing the first 70 minutes before being replaced by
Cesc Fàbregas in a 1–0 win against
Everton. He won his first Chelsea trophy on 1 March as the club defeated
rival club
Tottenham Hotspur 2–0 in the
League Cup final, coming on in the 76th minute for Willian. On 3 May, Cuadrado made his only third start since his move to Chelsea, in the
London derby match against
Crystal Palace, as
Ramires was taken ill before the game. At half-time, however, Cuadrado was substituted for
Mikel John Obi; Chelsea ended up claiming their fifth league title with a 1–0 victory. Three weeks later, in the final match of the season against
Sunderland, he won a penalty when fouled by
John O'Shea, on which
Diego Costa evened the score in an eventual 3–1 home win, but he was later substituted when he was injured in the final minute of the first half.
Juventus in 2017 On 25 August 2015, Cuadrado signed a season-long loan deal with
Juventus for €1.5 million. He was issued squad number 16. Five days later, he made his debut, as a 75th-minute substitute in a 2–1 defeat away against
Roma. On 31 October, Cuadrado scored his first Juventus goal against
Torino to secure a 2–1 win in extra time at the end of the
Derby della Mole. On 16 March 2016, Cuadrado scored his first ever
UEFA Champions League goal in a 4–2 away defeat against
Bayern Munich, in the second leg of the round of 16. On 21 May, he came off the bench to set-up
Álvaro Morata's match-winning goal against
Milan in the 110th minute of extra time of the
2016 Coppa Italia final, in
Rome's
Stadio Olimpico; Juventus' 1–0 victory enabled the club to secure the domestic double for the second consecutive season. Cuadrado returned to Chelsea on 30 June 2016 and played a few
friendlies for Chelsea, including the
2016 International Champions Cup. On 31 August, however, Cuadrado returned to Juventus on a three-year loan for €5 million per season, plus a conditional obligation to buy the full registration rights of Cuadrado from Chelsea for an additional €20 million (or €15 million and €10 million in the second and the third year of loan respectively), after certain sports related achievements. Chelsea would also receive a maximum of €4 million bonuses, making the fee potentially raise to €29 million. On 22 May 2017, it was announced that Cuadrado had joined Juventus on a permanent deal for a preset price of €20 million until 2020, after a clause in his contract had been triggered (winning the
Serie A mathematically in round 37). In the
2017 UEFA Champions League Final against defending champions
Real Madrid on 3 June, Cuadrado came on as a substitute for
Andrea Barzagli in the 60th minute, but was later controversially sent off after picking up two yellow cards, the second for an alleged stamp on
Sergio Ramos; Juventus lost the match 4–1. Following the arrival of
Cristiano Ronaldo from Real Madrid in 2018, Cuadrado allowed Ronaldo to wear the number 7 shirt, with Cuadrado reverting to number 16, saying on
Instagram "It is better to give than to receive [...] Blessings to Cristiano in this new adventure". During the
2019–20 season, under the club's new manager
Maurizio Sarri, Cuadrado was often deployed as an attacking right-back. Later that month, he extended his contract with the club until 2022. On 5 December 2020, Juventus won against
Torino by a score margin of 2–1, where Cuadrado assisted both the goals. On 15 May 2021, he scored a brace in a 3–2 home victory over Inter Milan. In the
2020–21 season, Cuadrado earned the title of best assistman of the
UEFA Champions League with six assists in six games. On 5 December, Cuadrado scored an
olympic goal in a 2–0 win against
Genoa. On 30 June 2023, Juventus bid farewell to Cuadrado after eight years with the club.
Inter Milan On 19 July 2023, Cuadrado joined
Inter Milan on a one-year deal. In December 2023, Cuadrado suffered a surgery-requiring achilles tendon injury. His injury was operated in
Turku, Finland by surgeon Lasse Lempainen in late December 2023.
Atalanta On 26 August 2024, Cuadrado joined as a free agent for fellow
Serie A side
Atalanta on a one-year contract.
Pisa On 6 August 2025, Cuadrado joined
Pisa on a free transfer, signing a one-year contract with the then recently promoted Serie A side. ==International career==