Tottenham Hotspur, a club known for flair, drama, and high expectations, has had its share of ups and downs in the Premier League era. While recent years have brought Champions League nights and title challenges (of sorts), there have also been seasons so frustrating that fans probably wanted to pretend they never happened. Let’s take a look back at some of Spurs’ worst Premier League campaigns—seasons that tested the patience of even the most loyal Lilywhites.

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1993/94: The Early Struggles

Tottenham finished a disappointing 15th in the 1993/94 campaign, just two seasons after the formation of the Premier League. Despite having attacking talent like Teddy Sheringham and a young Darren Anderton, the club was defensively weak, inconsistent, and tactically all over the place.

Off the pitch, the club was in turmoil. Financial mismanagement and a breach of FA rules regarding player contracts led to the threat of a points deduction (which was later overturned on appeal). It was a messy season in every sense. The club ended the season with 49 goals conceded and just 45 points—a far cry from the top-half ambitions fans had.

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1997/98: The Sugar-Venables Hangover

The 1997/98 season was one of the most chaotic in Tottenham’s modern history. Alan Sugar and Terry Venables’ fallout still cast a shadow over the club, and a revolving door of managers—including Gerry Francis, Christian Gross, and George Graham—meant there was little stability.

The season started disastrously, and Spurs were even bottom of the league by November. Christian Gross, the Swiss coach infamously introduced with an Underground ticket in hand, never quite got the dressing room onside. Tottenham eventually finished 14th, just four points above the relegation zone. The only bright spot? A young David Ginola beginning to sparkle.

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2003/04: The Post-Hoddle Hangover

Glenn Hoddle’s second spell in charge promised romance, but it ended in tears. Spurs finished a dreadful 14th in 2003/04, with just 45 points from 38 games and a shocking 57 goals conceded. This season felt like the club had no identity—there was no style, no substance, and no end product.

Freddie Kanouté and Robbie Keane provided some goals, but the team lacked cohesion. Defensively, it was a shambles, and midfield creativity was nearly non-existent. It felt like the club was drifting, unsure of what it wanted to be or how to get there.

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2007/08: The Juande Ramos Era Begins (Badly)

Tottenham actually finished 11th in 2007/08, which might not scream “worst ever” on paper. But considering the expectations going into the season—with the likes of Dimitar Berbatov, Robbie Keane, and Luka Modrić soon joining—the performance was incredibly underwhelming.

Martin Jol was harshly sacked early in the season, replaced by Juande Ramos, who had just won the UEFA Cup with Sevilla. But the league form never clicked under the Spaniard, despite a League Cup win. Spurs were a mess defensively and lacked steel in midfield. Ramos’ diet plans and harsh training didn’t help matters, and the writing was on the wall for the next season…

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2008/09: Two Points From Eight Games

If we’re talking pure embarrassment, 2008/09 under Juande Ramos might take the crown. Spurs started the season with two points from eight games—their worst ever start to a league campaign. The club was bottom of the table, players looked miserable, and Ramos seemed out of his depth in the Premier League.

Thankfully, Daniel Levy acted quickly. Ramos was sacked, and Harry Redknapp was brought in. “Wheeler-dealer” Redknapp turned the ship around, with key contributions from Luka Modrić, Jermain Defoe, and a young Gareth Bale (who hadn’t yet become a superstar). Spurs eventually finished 8th, but those first two months? Absolutely brutal.

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2013/14: The Post-Bale Spending Spree

When Gareth Bale was sold to Real Madrid for a then-world-record fee, Tottenham reinvested the money in “The Magnificent Seven”: Roberto Soldado, Paulinho, Nacer Chadli, Étienne Capoue, Vlad Chiricheș, Christian Eriksen, and Erik Lamela. Only Eriksen and Lamela (to a lesser extent) would become real assets.

Under André Villas-Boas, Spurs were overly cautious and toothless up front. AVB was sacked in December after a humiliating 5–0 defeat to Liverpool at White Hart Lane. Tim Sherwood took over, bringing some fight but also plenty of chaos. Spurs finished 6th, but given the money spent and the talent on paper, it felt like a complete failure.

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So, What’s the Worst One?

In terms of sheer hopelessness, 2008/09 under Ramos is probably the darkest chapter. The team looked relegation-bound, the players seemed lost, and the club had no identity. But 1997/98 and 1993/94 run it close, with both featuring off-pitch instability and underwhelming squads.

Tottenham fans have endured some painful seasons, but these lows also make the highs—like the Pochettino era or those electric Champions League nights—all the sweeter.

Because with Spurs, you’re always a few games away from either glory… or disaster. That’s just part of the ride.