A surprising new chapter in Denis Cheryshev’s career as former Real Madrid player moves to Krasava ENY Ypsonas
Former Real Madrid winger Denis Cheryshev has taken an unexpected step in his career after signing for FREEDOM24 Krasava ENY Ypsonas, the Cypriot club widely known for its Russian identity despite competing in Cyprus.
Now 35, Cheryshev brings a wealth of top-level European experience to Ypsonas. Born on 26 December 1990, he began his football education in Spain at Sporting Gijón’s academy, where his father Dmitri Cheryshev was playing.
From there, he joined Real Madrid Castilla, where he made 104 appearances and scored 22 goals, and went on to make a total of seven appearances for the first team.
Between 2012 and 2022, Cheryshev enjoyed a solid LaLiga career, representing Valencia, Sevilla and Villarreal, making 163 top-flight appearances and scoring 12 goals.
He later moved to Italy with Venezia in 2022/23, before spending last season in Greece with Panionios. His move to Ypsonas marks his first venture into Cypriot football.
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Russia World Cup heroics: four goals on home soil
Cheryshev’s career highlight came at the 2018 World Cup in Russia, where he unexpectedly emerged as one of the tournament’s standout performers. Initially not a guaranteed starter, he went on to score four goals, including memorable strikes against Saudi Arabia and Croatia, as Russia reached the quarter-finals on home soil.
In total, Cheryshev earned 33 caps for Russia, scoring 12 international goals, and featured across all youth levels before establishing himself with the senior side.
The infamous Copa del Rey fiasco with Real Madrid
Despite his pedigree, Cheryshev’s time at Real Madrid is often remembered for an unfortunate off-field episode. In December 2015, Madrid were thrown out of the Copa del Rey after fielding Cheryshev against Cádiz while he was serving a suspension accumulated during a loan spell.
The incident became one of the most embarrassing administrative errors in the club’s modern history and overshadowed what had otherwise been a promising spell for the winger at the Bernabéu.
Krasava ENY Ypsonas: The ‘Russian’ club in Cyprus
While Denis Cheryshev’s name naturally draws attention, his new club is arguably just as intriguing. Krasava ENY Ypsonas are based in Cyprus, but their identity, ownership and fanbase are unmistakably Russian – making them one of the most unusual stories in European football’s lower leagues.
The club is owned by Yevgeny Savin, a former professional footballer turned YouTuber known online as Krasava. Savin became one of the most high-profile Russian sporting figures to publicly oppose the invasion of Ukraine, a stance that ultimately forced him into exile.
After leaving Russia, he relocated his Krasava football project abroad, settling in Cyprus as a base where the club could continue to operate independently of Russian football authorities.
Despite their relatively recent formation, Ypsonas have risen rapidly through the Cypriot football pyramid, fuelled by outside investment, professional infrastructure and a clear long-term vision.
The club competes under the official name FREEDOM24 Krasava ENY Ypsonas, with “Freedom” branding deliberately reflecting Savin’s political stance and the club’s positioning as a safe haven for players and staff unwilling or unable to remain in Russia.
Krasava have also built a strong international following, driven largely by Savin’s online presence and the documentary-style content he produces around the club.
Matches, training sessions and behind-the-scenes moments are shared with millions of viewers, turning Ypsonas into a globally recognised project despite their modest domestic status.
The signing of a player with Cheryshev’s pedigree is another statement of intent – and a sign that this once-obscure Cypriot side is aiming to grow far beyond its traditional limits.