Tottenham Hotspur, a club with a rich and storied history, has seen its fair share of triumphs and disappointments over the years. While the Lilywhites have enjoyed many successes on the pitch, they have experienced their fair share of setbacks and disappointments. From expensive transfers that failed to live up to expectations to managerial appointments that left fans scratching their heads, Tottenham has had its fair share of flops throughout its history. Here, we look at the top three greatest flops in Tottenham Hotspur's history.

3. Vincent Janssen

Signed from AZ Alkmaar in 2016 for a fee reported to be in the region of £17 million, Vincent Janssen was expected to provide competition for Harry Kane and bolster Tottenham's attacking options. However, the Dutch striker struggled to make an impact and endured a difficult spell in North London. Janssen managed just two goals in 27 Premier League appearances for Tottenham and failed to establish himself as a regular starter. Despite being handed numerous opportunities to impress, Janssen failed to deliver on the pitch and was eventually loaned out to Fenerbahçe and then sold to Mexican side CF Monterrey in 2019.
Janssen's time at Tottenham was characterized by frustration and disappointment as he struggled to adapt to the demands of English football. His departure was met with a sense of relief, as Tottenham fans were eager to move on from a failed experiment and focus on building for the future.

2. Roberto Soldado

When Tottenham signed Roberto Soldado from Valencia for a club-record fee of £26 million in 2013, expectations were sky-high. The Spanish striker had a reputation as a clinical finisher and was expected to solve Tottenham's long-standing issues in front of goal. However, Soldado struggled to adapt to the pace and physicality of the Premier League and endured a torrid time in North London. Despite showing flashes of his quality, including a memorable Europa League hat-trick against Anzhi Makhachkala, Soldado managed just 16 goals in 76 appearances for Tottenham. He was eventually sold to Villarreal in 2015, having failed to live up to the lofty expectations placed upon him.

Soldado's time at Tottenham was marked by missed chances and frustration as he struggled to replicate the form that had made him such a sought-after talent in Spain. His departure was met with disappointment, as Tottenham fans had hoped for much more from their record signing.

1. Sergei Rebrov

Signed from Dynamo Kyiv in 2000 for a then-club record fee of £11 million, Sergei Rebrov arrived at White Hart Lane with high expectations. The Ukrainian striker had established himself as one of the most prolific goalscorers in Europe during his time at Dynamo Kyiv. Still, he struggled to adapt to the rigors of the Premier League. Rebrov managed just ten goals in 59 league appearances for Tottenham, failing to replicate the form that had made him such a sought-after talent. Despite occasionally showing glimpses of his talent, Rebrov failed to justify his hefty price tag and was sold to West Ham United in 2004.

Rebrov's time at Tottenham was frustrated and disappointed as he struggled to find his best form in the Premier League. His departure was met with a sense of resignation, as Tottenham fans had hoped for much more from their record signing.

HONORABLE MENTION: George Graham

While not a player, George Graham's tenure as manager of Tottenham Hotspur is widely regarded as one of the darkest periods in the club's history. Graham arrived at White Hart Lane in 1998 with a stellar reputation, having enjoyed great success at Arsenal, but his tenure at Tottenham was marred by controversy and underachievement. Graham's pragmatic style of football was at odds with Tottenham's tradition of attacking play, and he struggled to win over the fans with his negative tactics. Despite leading Tottenham to League Cup success in 1999, Graham was sacked in 2001 after a string of poor results and amid allegations of financial misconduct.

Graham's time at Tottenham is remembered more for the discord and underwhelming performances than for notable achievements on the pitch. His departure marked the end of a tumultuous chapter in the club's history, and Tottenham fans were relieved to see the club move on from the Graham era.

While Tottenham Hotspur has enjoyed many successes throughout its history, the club has endured its fair share of disappointments and failures. From expensive signings that failed to live up to expectations to managerial appointments that proved disastrous, Tottenham has experienced several high-profile flops over the years. While these setbacks may have been painful at the time, they have ultimately helped to shape the club's identity and serve as a reminder of the highs and lows of football.