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With Arrizabalaga struggling to stay in form during the 2019–20 Premier League season, Caballero was selected as the starting goalkeeper for Chelsea in a cup match against Hull City in late January 2020. Caballero was then the starting goalkeeper for the next four league matches and a Champions League match before Arrizabalaga returned. On May 20, 2020, Caballero had his contract with Chelsea extended by one more year.

On 24 February 2019, during the 2019 EFL Cup Final against cup holders Manchester City, with the match at 0–0 and a penalty shootout imminent, Chelsea goalkeeper Kepa Arrizabalaga refused to be substituted off for Caballero to face his old club as the team went on to lose 3–4.

Caballero made his senior debut for Argentina in 2018. He represented the nation at the 2018 World Cup, and was also a non-playing member of the squads that won a gold medal at the 2004 Summer Olympics and finished runners-up at the 2005 Confederations Cup.

On 17 January 2018, Caballero saved a penalty from Nélson Oliveira in the shootout of a third round FA Cup replay win over Norwich City, which had finished 1–1 after extra time. Due to an ankle injury to first-choice Thibaut Courtois, he made his Premier League debut away to Brighton & Hove Albion two days later, in a 4–0 success.

Caballero was an unused member for the senior squad at the 2005 FIFA Confederations Cup. In November 2014, he was called by manager Gerardo Martino for friendlies against Croatia and Portugal. He only won his first cap nearly four years later at the age of 36, starting in a 2–0 defeat of Italy on 23 March 2018 in another exhibition game, played in Manchester.

Caballero was included in the final squad for the 2018 FIFA World Cup in Russia. He started the tournament due to the injury of habitual first-choice Sergio Romero, and made his debut in the competition on 16 June in a 1–1 group stage draw against Iceland. In the next match against Croatia, his mistake handed the opposition the first goal in a 0–3 defeat, and he was subsequently dropped by manager Jorge Sampaoli in favour of Franco Armani for the team's final group match against Nigeria, which ended in a 2–1 win; he also did not feature in the round of 16 game, a 3–4 loss to France.

On 1 February 2017, Caballero replaced Bravo. On his return to the starting XI, he kept a clean sheet in a 4–0 win over West Ham United at the London Olympic Stadium. Late into the month, in a 5–3 Champions League round of 16 win over Monaco, he saved a penalty from Radamel Falcao.

On 25 May 2017, it was announced Caballero would leave the club on the expiry of his contract, which occurred on 30 June.

On 1 July 2017, Caballero signed for title holders Chelsea on a free transfer. He made his competitive debut on 20 September, in a 5–1 home win against Nottingham Forest for the League Cup.

Following the appointment of manager Pep Guardiola in the 2016 off-season, Caballero became the starter over Hart. Soon after, with the signing of Claudio Bravo, he returned to his backup role.

On 19 October 2016, Caballero appeared as a substitute in a 0–4 defeat by Barcelona at the Camp Nou in the group stage of the UEFA Champions League. After replacing the red-carded Bravo in goal, he saved a penalty from Neymar in the 87th minute of the match. Two weeks later, he deputised for the suspended Bravo in the 3–1 home win over the same opponent for the same competition.

Caballero's third league match was on 26 September 2015, a 1–4 defeat at Tottenham Hotspur which was described as 'a day to forget'. Throughout the season, he was first-choice in the League Cup, receiving criticism in the national press before the final following the 1–5 loss to Chelsea in the FA Cup where he was adjudged to be at fault for two goals; in the decisive match at Wembley Stadium, he saved three attempts in the 3–1 penalty shootout triumph against Liverpool, and Pellegrini subsequently said he would rather lose the match to keep his word, whilst several pundits added that both player and manager deserved an apology with some remarking the performance was a lesson in loyalty.

He spent most of his career in Spain, representing Elche and Málaga and competing in La Liga with the latter club. In the summer of 2014 he signed for Manchester City, helping them win the 2016 League Cup.

On 8 July 2014, Caballero signed a three-year deal with Manchester City, for a fee believed to be in the region of £6 million excluding add-ons. He reunited at his new club with former Málaga manager Manuel Pellegrini, and his competitive debut came on 10 August in the 2014 FA Community Shield, playing the full 90 minutes in a 0–3 loss to Arsenal at Wembley Stadium; a week later, in the Premier League opener, he was an unused substitute at Newcastle United.

Caballero's second official appearance for City occurred on 24 September 2014, in the 7–0 home routing of Sheffield Wednesday for the Football League Cup. He made his first league appearance away against Hull City three days later, relegating longtime incumbent Joe Hart to the bench in a 4–2 win.

On 18 January 2012, Caballero signed a contract extension, tying him to the club until 2016. On 25 March, playing against Espanyol, he fractured his left hand early into the game, being sidelined for the rest of the season.

Caballero returned to full fitness for 2012–13, featuring in all but two games and helping the Boquerones to the sixth position. Goal.com named him as the best player in his position for the campaign. At the end of the following season, he was nominated as the best goalkeeper in the league alongside Thibaut Courtois of Atlético Madrid and Keylor Navas of Levante.

On 10 February 2011, Caballero was transferred to Málaga in La Liga for €900,000 and two-and-a-half years, as an emergency transfer – after the transfer deadline of 31 January – due to a serious knee injury to Sergio Asenjo (their previous starter, Rubén, was also unavailable due to physical problems); he made his league debut on 20 February, starting in a 1–1 draw at Villarreal, and played all the matches until the end of the campaign, with the Andalusians finally escaping relegation.

On 1 October 2011, Caballero entered Málaga's history books as he kept his goal clean for 480 minutes, beating the club's previous record of 429 held by Pedro Contreras since the 2001–02 season. On 16 October, he was sent off midway through the first half of an away fixture against Levante after touching the ball with his hands just outside the box – the hosts eventually won it 3–0.

Caballero joined Elche of Spain in 2004, and when his daughter was diagnosed with cancer he agreed to a brief loan spell back in his country with Arsenal de Sarandí to care for her. With the former, after a rough first season, he went on to become the undisputed starter, appearing in nearly 200 Segunda División games.

Born in Santa Elena, Entre Ríos, Caballero started his playing career with Boca Juniors in 2001, where he won three major titles in 2003. On 14 December of that year he witnessed – from the bench – his team beat A.C. Milan 3–1 on penalties, in the 2003 Intercontinental Cup.

Caballero played for Argentina at under-20 level, helping the nation win the 2001 FIFA World Youth Championship by playing in the competition's last two games. In 2004, he was picked for the gold medal-winning squad at the 2004 Summer Olympics as backup to Germán Lux (also first-choice in the previous tournament).

Wilfredo Daniel "Willy" Caballero Lazcano (born 28 September 1981) is an Argentine professional footballer who plays as a goalkeeper for Premier League club Chelsea and the Argentina national team.