1. Roberto Soldado
Roberto Soldado Rillo is a professional Spanish footballer who plays as a forward for Segunda División club Levante. He gained recognition through Real Madrid's youth system, although he only played 27 official matches for the senior team, scoring 4 goals. However, he became a more regular player in La Liga, netting goals for Osasuna, Getafe, and Valencia, which led to his £26 million transfer to Tottenham Hotspur.
After dominating in Spain with Valencia, Roberto Soldado's move to Tottenham Hotspur in 2013 was expected to elevate him to the highest echelons of world football. Yet, seven goals in 52 matches only left fans disappointed, and his underwhelming performance nearly turned Spurs into a laughingstock. Soldado scored his only goal against relegation-threatened Cardiff City on March 2, 2014, his first after nine games.
Soldado's poor form was so severe that Spurs had no choice but to call upon a random youngster from the academy to save them. That youngster turned out to be Harry Kane, who might not have thrived had Soldado's career been successful. He only scored six goals in his first season with Spurs, with just two from open play, earning a spot on The Telegraph's list of "10 Worst Premier League Signings of the Season".

2. Ángel Di María
Ángel Di María is a professional Argentine footballer currently playing for Juventus in Serie A and the Argentina national team. Known for his agility, speed, and dexterity, Di María has been regarded as one of the greatest players of his generation and is considered one of the greatest Argentine players of all time.
When Ángel Di María joined Manchester United from Real Madrid for a record £59.7 million, he was expected to be a top-tier player, but reality turned out to be quite different. The Argentine was handed the iconic No. 7 shirt, but it gathered dust at Old Trafford as he only scored 3 goals in 27 matches. Di María was substituted due to a hamstring injury in the 13th minute during United's 3–0 loss to Hull City on November 29, and only featured once as a substitute in the following seven games.
Di María was sent off on March 9 when Manchester United lost 1–2 at home to Arsenal in the FA Cup quarterfinals, receiving a yellow card for diving and for grabbing referee Michael Oliver’s shirt, even though Wayne Rooney had earlier equalized for the team. A combination of injuries, off-field issues, and a strained relationship with Louis van Gaal contributed to his struggles, but it was undeniable that Di María simply wasn’t good enough. By the end of the season, The Daily Telegraph ranked Ángel Di María as one of the worst signings of the year.

3. Juan Cuadrado
Juan Cuadrado is a Colombian professional footballer currently playing for Serie A club Juventus and the Colombia national team. He is known for his direct style of play, which includes both speed and impressive dribbling skills. However, when he joined the Premier League, his reputation didn’t quite live up to expectations.
While playing for Fiorentina, Juan Cuadrado became one of the most exciting wingers in Serie A, and his performances with Colombia in the 2014 World Cup further boosted his reputation. He was ready for the next step, and Chelsea approached him, bringing him to England in early 2015. Unfortunately, things quickly unraveled. He failed to impress in his brief appearances, never earned a starting spot, and made Chelsea worse when he was on the pitch. It was a disaster.
Five days after signing, Cuadrado made his Chelsea debut as a substitute for Willian in the final 10 minutes of a 2–1 victory against Aston Villa. On February 11, he played his first match at Stamford Bridge, featuring for 70 minutes before being replaced by Cesc Fabregas in a 1–0 win over Everton. He spent only six months in England before being loaned to Juventus for two years, eventually moving to Italy permanently.

4. Eliaquim Mangala
Eliaquim Mangala is a French footballer who plays as a center-back. In 2014, he became the most expensive defender in Premier League history when he signed for Manchester City for £42 million — a deal that seemed reasonable at the time. The Frenchman had been a dominant force at his previous club Porto and appeared to be a real star. However, City quickly realized, after just two seasons, that they had been duped. Mangala made more mistakes than valuable contributions, and it seemed like he was occasionally terrified of playing the game.
Mangala debuted in Man City’s fifth match of the Premier League season, a 1–1 draw at home against Chelsea on September 21. Just six days later, a own goal and a penalty conceded by Mangala helped Man City lose 2–0 to Hull City, although they eventually won 4–2. On November 30, Mangala was sent off with two yellow cards in a 3–0 victory over Southampton. After several unsuccessful loan spells, Mangala was transferred to Valencia on a free transfer in 2019, ending one of the most disappointing stints in English football.

5. Gonzalo Higuain
Gonzalo Higuain is a former professional footballer from Argentina who played as a striker. Nicknamed El Pipita or Pipa, Higuain was a powerful forward known for his sharp goal-scoring instincts, strong physical presence, and attacking movements. In 2019, Chelsea’s manager at the time, Maurizio Sarri, was determined to turn a weary Gonzalo Higuain back into the superstar he was during his time with Napoli. However, that never materialized. In early December 2010, Higuain was diagnosed with a lumbar disc herniation.
During his six-month stint in England, Higuain scored just five goals, three of which were against teams facing relegation. Two of his other goals came against teams near the bottom of the table, which says a lot about the 'quality' he brought to Stamford Bridge. Higuain's form was inconsistent, although he did finish the season on a strong note. Once considered one of the brightest prospects in world football thanks to his dramatic performances and last-minute goals, his penalty-taking ability started to decline as his career progressed. Notable examples include his poor performances in cup finals and critical UEFA Champions League and UEFA Europa League matches.

6. Robinho
Robson de Souza, better known as Robinho, is a former professional footballer from Brazil who played as a forward. At the age of 15 in 1999, Robinho was selected by Brazilian legend Pelé as his successor, and in 2002, Robinho helped lead Santos to their first Campeonato Brasileiro title since Pelé himself played for the club. He went on to win another title with Santos, two with Spanish club Real Madrid, and an Italian Serie A title during his first season at Milan.
Robinho's time in England began when he told reporters that he was excited to join Chelsea, although Manchester City had just signed him for £32.5 million in 2008. Things started well, but Robinho soon forgot how to play football. He was plagued by constant injuries, leading to a loan move back to Santos in January 2010, failing to live up to expectations.
Robinho's form made Chelsea fans feel lucky to have avoided a dangerous player, but countless other failed transfers by The Blues quickly brought them back to reality. His second season at Manchester City wasn't much better. He missed three months due to injury and only played 12 matches in total (10 in the Premier League), scoring just one goal (against lower league Scunthorpe United in the FA Cup). As a result, he opted to leave the club during the January transfer window.

7. Davor Suker
One of Croatia's finest players, Davor Šuker lit up La Liga for eight years from 1991 to 1999, scoring numerous goals for both Sevilla and Real Madrid. He also led Croatia to the semifinals of the 1998 World Cup, which clearly made him a player worth considering. Arsenal tried to lure him away from Madrid, but soon regretted their decision. The former Ballon d'Or runner-up scored eight goals in his first five league matches, and was allowed to join West Ham after just one season.
Davor Šuker scored 10 goals in 29 appearances. In the 1998–99 season, his presence at Real Madrid diminished, despite his excellent performance in that summer's World Cup. This became evident when he only played 19 league games, scoring a total of four goals. At the end of the season, he decided to leave the club, marking the conclusion of his eight-year stay in Spanish Primera, where Šuker netted 114 goals in 239 appearances.
Šuker joined the FA Premier League club Arsenal for the 1999–2000 season. He made his league debut on August 22, 1999, in a 2–1 loss to Manchester United at Highbury. After two more substitute appearances, he started in Arsenal's 3–1 victory over Aston Villa. At West Ham United, Šuker only made 11 league appearances during the season, scoring two goals against Manchester United and Sunderland. With the Hammers, he spent much of his time recovering from injury, adding just two more goals before moving to Germany.

8. Juan Sebastian Veron
Argentine international player Juan Sebastian Veron had an outstanding career in Italy with both Parma and Lazio, and appeared destined to become one of the best midfielders in the world. After the 2000–01 season, he moved from Lazio to Manchester United on July 12, for a £28.1 million transfer fee, making it the most expensive deal in English football at the time, and he became the first player outside of UEFA to break England's transfer record.
Veron's first season at Old Trafford started well. In September 2001, he scored in three out of four Manchester United matches, including a goal and an assist in a 5–3 comeback win against Tottenham Hotspur, which ultimately earned him the Premier League Player of the Month award. However, as the season wore on and fatigue set in, his performances began to decline. He struggled to adjust to the Premier League's faster pace, where he no longer had the same space and time on the ball.
The pressure mounted on Juan Sebastian Veron as he began his second season at Old Trafford, but his performances improved significantly. However, an injury meant that he missed most of the latter part of the season. His transfer fee to Chelsea was just half of the record transfer fee that he had commanded just two years prior. The Times listed both Veron's transfers to Manchester United and Chelsea among the 50 worst transfers in Premier League history.

9. Falcao
Falcao was once hailed as one of the most dangerous forwards in football. Known as 'El Tigre,' he dominated both Porto and Atlético Madrid from 2009 to 2013, and his early days with Monaco in the 2013/14 season began impressively. Unfortunately, injury struck. Manchester United took a gamble in 2014, hoping Falcao would regain his form, but he could only manage four goals in 26 appearances for the Red Devils. His time in England was considered a failure, leading many to believe he had no future in top-flight football. Yet, Chelsea surprisingly signed him to a significant contract.
Falcao was regarded as a natural-born goal scorer, capable of finishing from almost any situation. His controversial transfer to Ligue 1 newcomers Monaco in 2013, with a record-breaking fee of 60 million euros, raised eyebrows, despite interest from several top European clubs. During the second half of his first season, an ACL injury sidelined him for six months; he then spent two more seasons on loan in the Premier League with Manchester United and Chelsea.
Upon his return to Monaco in the summer of 2016, Falcao regained his best form and led them to their first Ligue 1 title in 17 years. He moved to Galatasaray in 2019 and returned to La Liga in 2021 with Rayo Vallecano. Falcao holds the record for being Porto's all-time top scorer in European club competitions, setting a record for the most goals (17) in a European campaign in 2011 and becoming the first player to win the Europa League back-to-back with two different clubs.

10. Andriy Shevchenko
Andriy Shevchenko won the 2004 Ballon d'Or. He was the top scorer in the Champions League during both the 1998/99 and 2005/06 seasons. Shevchenko also earned a spot in the 2005 FIFPro World XI. However, his time in the Premier League could be considered one of the biggest disappointments in its history. Brought to Chelsea by Roman Abramovich in 2006, Shevchenko’s poor form at Stamford Bridge led fans to have low expectations for him.
His 2006-07 season was cut short due to injury and hernia surgery. He missed the Champions League semifinal against Liverpool and the FA Cup final against Manchester United at the new Wembley Stadium on May 19, 2007. Shevchenko made his first appearance of the 2007-08 season in a 0-0 draw against Blackburn Rovers at home, stepping in for the injured Didier Drogba. Three days later, he scored his first goal of the season, equalizing for Chelsea against Rosenborg. This match also turned out to be José Mourinho’s final game as Chelsea manager.
Throughout the season, Shevchenko was a regular starter due to injuries and the appointment of Avram Grant following Mourinho’s departure. Shevchenko was not frequently used in the starting lineup at Chelsea, and with Luiz Felipe Scolari’s appointment, he was considered surplus to requirements. As a result, Milan’s vice president, Adriano Galliani, offered to bring Shevchenko back to San Siro, and he was loaned back to his former club for the 2008-09 season.
