O'Higgins Cuevas began his career at
Primera División de Chile club
O'Higgins. He progressed from the club's youth level all the way to the senior team. In 2011, he was promoted to the senior team, making his debut on 8 May in a 5–1 away loss to
Colo-Colo at the
Estadio Monumental. Cuevas has continued to appear since it, particularly in
Copa Chile games. In November 2012, it was reported that Cuevas had held a successful trial with
Premier League club
Chelsea following a number of impressive performances for the
Chilean under-20 team. In 2013, after a season at the reserve team, he was considered by
Eduardo Berizzo to play the
Torneo Transición, who chose him after a well
South American Youth Football Championship in Argentina with the national under-20 side. He made seven appearances (the most of those as
left back) and before the
FIFA U-20 World Cup, on 23 July, Cuevas completed a five-year contract with Chelsea which will keep at
Stamford Bridge until 2018. The transfer fee paid to O'Higgins was reported as £1.7 million.
Chelsea After his successful move, Cuevas joined the club's pre-season and stayed training with the first adult team alongside other youngsters players under the orders of
José Mourinho before being sent on season long loan to Dutch
Eredivisie club
Vitesse. There he linked up with fellow Chelsea loanees
Patrick van Aanholt,
Gaël Kakuta,
Lucas Piazon,
Tomáš Kalas,
Sam Hutchinson and
Christian Atsu.
Loan to Vitesse On 1 September 2013, Cuevas made his first appearance on the bench in the match against
AZ, although he was an unused substitution as Vitesse drew 1–1. On 1 September 2013, he again made an appearance on the bench in the match against
PEC Zwolle, but remained unused. Cuevas failed to make a single first team appearance before Vitesse decided to cancel his loan in February.
Loan to FC Eindhoven On 7 February 2014, it was announced that Cuevas would spend the rest of the season on loan with
FC Eindhoven in the Dutch
Eerste Divisie. Later that day, he made his debut, coming off the bench and replacing
Torino Hunte after the first half in a match against
Almere City which ended in a 2–1 loss for Eindhoven. On 28 March, he scored his first goal for the club – and his first professional goal – in a 4–0 win over
Sparta Rotterdam. He finished the season with 13 appearances and one goal.
Loan to Universidad de Chile On 30 June 2014, Cuevas was sent on a season long loan to
Universidad de Chile. He made his debut on 13 February 2015 against
Unión Española, which ended in a 2–1 loss for Universidad de Chile. Cuevas made a total of six appearances with only four league appearances during his time back in his home country.
Loan to Sint-Truiden On 10 August 2015, Cuevas was sent on a season-long loan to Belgian side
Sint-Truiden along with fellow Chelsea youth player
Joao Rodríguez. On 16 August 2015, he made his debut off the bench in the 62nd minute, replacing
Yannis Mbombo in the match against
Gent, a 1–0 defeat. On 21 November 2015, he scored his first goal for Sint-Truiden in their 2–1 away defeat against
Waasland-Beveren, netting the opener of the fixture in the 9th minute. On 31 August 2016, Cuevas returned to Sint-Truiden for another season-long loan.
Huachipato On 1 July 2017, Cuevas agreed to return to Chile to join
Primera División side
Huachipato and a month later joined Dutch side
Twente on a season-long loan. On 14 April 2018, he became the joint record holder for most yellow cards in a single Eredivisie season after getting his 12th yellow card of the season against
ADO Den Haag. Following a season at Twente, Cuevas joined
Austria Wien in July 2018 on a season-long loan, with an option to buy.
Universidad Católica On 31 January 2022, Cuevas joined
Universidad Católica on a permanent basis. ==International career==