[6] 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.

[9] On 27 November, he played his official game with the first team, in a 3–0 home win (7–1 on aggregate) over Alcoyano in the round of 32 of the Copa del Rey.

[10][11] In September 2013, Cheryshev was loaned to fellow league club Sevilla for the remainder of the campaign with the possibility of a permanent deal.

[12][13] 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.

[16][17][18] 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.

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.

[3][42] 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.

[43] 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; after just five minutes on the pitch, he had to be stretchered off in an eventual 1–0 loss.

[51] 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.