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On 29 June 2019, Cheryshev joined Valencia permanently for a fee of €6 million.

After an absence of more than two years, Cheryshev appeared for the national team again on 27 March 2018 in a friendly with France. On 11 May, he was included in an extended squad for that year's World Cup, also being named as one of the final 23 players. He made his debut in the competition on 14 June, replacing the injured Alan Dzagoev midway through the first half of the group stage opener against Saudi Arabia in Moscow and scoring twice in a 5–0 win. He scored his third goal in the tournament against Egypt in a 3–1 victory, adding another in the quarter-finals when he curled a strike past Croatia's Danijel Subašić from just outside the 18-yard area to open the scoring, but in an eventual 3–4 penalty shoot-out loss.

On 1 February 2016, Cheryshev was loaned to Valencia until June. He made his debut two days later, coming on as a second-half substitute in 7–0 away loss against Barcelona in the semi-finals of the domestic cup. He scored his first and only goal on 13 February, when he headed home in a 2–1 win over Espanyol at the Mestalla Stadium.

On 15 June 2016, Cheryshev returned to Villarreal on a permanent deal where he signed a contract until 2021. On 14 August 2018 he returned to Valencia on loan, scoring twice during the season to help to a fourth-place finish.

Returned to the Santiago Bernabéu Stadium, Cheryshev made top flight debut for Real Madrid on 19 September 2015, playing 13 minutes in a 1–0 defeat of Granada. He scored his first competitive goal for them on 2 December, featuring 45 minutes in a 3–1 away victory over Cádiz in the Spanish Cup's round of 32. However, his appearance in the match drew controversy as he was ineligible for selection after having collected three yellow cards in the previous edition of the tournament, and resulted in Real Madrid being expelled from the tournament. President Florentino Pérez claimed that the Royal Spanish Football Federation had not informed the club that the player was suspended and challenged the action taken against the team, though he was unsuccessful.

Cheryshev scored on his debut for Villarreal on 24 August 2014, netting the second goal in a 2–0 win at Levante. Having recovered from the injuries which plighted his time at his previous team, he thrived at El Madrigal and netted seven times in 40 appearances across all competitions.

In September 2013, Cheryshev was loaned to fellow league club Sevilla for the remainder of the campaign with the possibility of a permanent deal. As a result of persistent injury concerns, he made only four league appearances and the Andalusians opted not to exercise the option, with the player joining Villarreal on loan for 2014–15 instead.

Cheryshev played his first competitive game on 14 August 2013, when he came on as a half-time substitute in a 2014 FIFA World Cup qualifier against Northern Ireland in Belfast. However, after just five minutes on the pitch, he had to be replaced due to injury, in an eventual 0–1 loss; he was called up to a provisional 25-man squad for the finals on 16 May 2014, being the only player present not playing his club football in Russia. He was, however, left out of Fabio Capello's final list and also later missed the UEFA Euro 2016 tournament due to injury.

Having earned 45 caps and scored 23 goals in its youth categories, Cheryshev made his debut for Russia in 2012. He was a participant at the 2018 World Cup, scoring four goals as the team reached the quarter-finals.

Cheryshev made his debut in division two on 17 August 2012, playing the full 90 minutes in a 1–2 away loss against Villarreal. On 27 November, he made his official debut for the first team in a 3–0 home win (7–1 on aggregate) over Alcoyano in the season's Copa del Rey.

Prior to making his international debut with Russia, Cheryshev was also eligible to represent Spain as he held dual nationality. In a 2011 interview with Marca he indicated that he felt more Spanish than Russian, but accepted a call up to the Russian team in November 2012. He made his debut eight days later in a 2–2 friendly draw with the United States, the same opposition his father Dmitri had played against 20 years earlier.

A youth product of Real Madrid, he made his senior debut for the reserves in 2009 and with the first team in 2012. He then had loan spells at Sevilla, Villarreal and Valencia before joining Villarreal permanently in 2016, and returned to Valencia on loan two years later.

Cheryshev joined Real Madrid in 2002, and completed his formative years in their academy. Still a junior, he appeared in nine Segunda División games with Real Madrid Castilla during the 2008–09 season; it was also during this time he formed a long-lasting friendship with future Spanish national team player Nacho.

Born in Nizhny Novgorod, Russian Soviet Federative Socialist Republic, Soviet Union, Cheryshev started his career at Sporting de Gijón, where his father Dmitri was playing at the time. He soon followed him to his next club, Burgos, entering locals CD Burgos Promesas 2000 at the age of 9.

Denis Dmitriyevich Cheryshev (Russian: Денис Дмитриевич Черышев ; born 26 December 1990) is a Russian professional footballer who plays as a left winger for Spanish club Valencia CF and the Russian national team.