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Tottenham Hotspur’s cursed season: a timeline of misery

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It couldn’t be worse.

Wolverhampton Wanderers v Tottenham Hotspur - Premier League Photo by Charlotte Wilson/Offside/Offside via Getty Images

With our world in crisis, we could be forgiven for forgetting about Tottenham Hotspur’s woes for a while. Still, some just can’t help it. If, like me, you’ve been mulling over how it all went wrong for Spurs even as you contemplate the end of the world as we know it, why not wallow in it for a moment?

Consider the following: on the eve of Tottenham’s first Premier League game, aspirations were at an all-time high: Spurs had found their way to a Champions League final the previous season, and with the signings of Tanguy Ndombele and Giovani Lo Celso, it seemed the squad was finally receiving the investment it needed. When I read Joel Wertheimer’s even-handed analysis of the team’s prospects in advance of the 19-20 season, I trusted that the new signings would bolster our lagging midfield, some summer coaching would fix the holes in our defense, and believed in Kane, Son, and Dele’s form and quality.

In short, I was optimistic. Instead, everything—everything—imaginable went wrong. All sorts of unlikely things happened, time and time again, always with Tottenham on the losing end. After eight months of bad luck ending in a global crisis on a greater scale than many have seen in their entire lives, let’s look back on what made this truly a cursed season.

August 8, 2019: Ryan Sessegnon transfers from Fulham with a hamstring injury

Denmark U21 v England U21 - International Friendly - Blue Water Arena Photo by Simon Cooper/PA Images via Getty Images

This one was to be expected, since Sessegnon had been injured since June when his transfer was completed. Still, signing an injured player was an omen of a season which saw the team disrupted, time and time again, by injury. Spurs had to wait until November for Sess to regain match fitness, and without a summer of preseason and exposure in early matches, he barely found time in the squad after that.

September 5, 2019: Giovani Lo Celso is injured in an international friendly before ever starting a game for Spurs

Tottenham Hotspur Press Conference And Training Session Photo by Alex Morton/Getty Images

The second summer signing disrupted by an injury woe, Giovani Lo Celso is Tottenham’s joint-record signing along with Tanguy Ndombele, and heading into the 19-20 season buzz around him was high. Pochettino seemed to be introducing him slowly to the Spurs side, which was perhaps a wise decision since he had very little time to acclimate to Spurs after his late-summer signing. Early substitute appearances against Manchester City, Newcastle, and Arsenal had excited fans, and then—in the first of many misfortunes for the team this year—Lo Celso picked up a groin injury in a friendly against Chile. He was out with the injury itself for most of September and October, and then it took a few games after his return to finally earn a first start, against Sheffield on November 9. Only in early January did Lo Celso become a regular starter, and this early injury right as he was getting settled certainly prevented either manager from being able to trust his quality sooner. As we know now, Lo Celso is one of Spurs’ best, and having him in the side sooner might have helped things turn out differently this season.

October 5, 2019: Hugo Lloris dislocates his elbow as he fumbles a save and concedes against Brighton in the second minute.

Brighton & Hove Albion v Tottenham Hotspur - Premier League Photo by Bryn Lennon/Getty Images

Spurs visited Brighton and Hove Albion expecting to add to their points tally. Instead, Lloris made a poor error in the second minute, losing his balance as he tried to catch a cross and landing awkwardly on his elbow as Maupay headed in from close range. Tottenham never recovered from the shock, and Brighton ran away with the game. The final score was 3-0, but the bigger blow was that Lloris was out through mid-January, one of Spurs’ greatest personnel losses in a season defined by them.

November 3, 2019: Son Heung-min inadvertently brings about one of the most gruesome football injuries in recent memory, costing Spurs a much-needed win.

Everton FC v Tottenham Hotspur - Premier League Photo by Michael Regan/Getty Images

Son’s slide tackle from behind on Andre Gomes was petulant, a retaliation for an earlier aggression by Gomes on the South Korean. But he couldn’t have imagined what would happen next as Gomes got his boots caught in the turf, stumbled into Serge Aurier, and fractured and dislocated his right ankle, leaving his foot hung at a right angle from his leg. Son and Aurier looked like they’d seen a ghost. After Son was sent off, Cenk Tosun grabbed a last-gasp equalizer that cost Tottenham two points.

November 19-20, 2019: Mauricio Pochettino is sacked, Jose Mourinho appointed his replacement

Tottenham Hotspur v Olympiacos FC: Group B - UEFA Champions League Photo by Catherine Ivill/Getty Images

People have strong feelings about this double whammy. The #PochOut brigade was gratified by it, others felt that the team’s poor form was beyond Poch’s control. Some think Mourinho remains a tactical genius, while others regard him as a sexist egomaniac past his managerial prime. No matter how you come down on the two gaffers, bidding farewell to Pochettino under such dismal circumstances was a tragic end to an important era in recent Spurs history. Likewise, replacing him with a manager known for self-aggrandizement and leaving teams in ashes meant an abrupt shift in mood among Spurs fans.

December 22, 2019: Antonio Rudiger is racially abused by Tottenham supporters

Chelsea FC v Tottenham Hotspur - Premier League Photo by James Williamson - AMA/Getty Images

Rudiger insists there was racial abuse coming from a Tottenham section when Chelsea visited north London, and while a subsequent investigation could not find enough evidence to go forward, it’s hard to believe he fabricated the entire thing. This was the second time in just over a year that somebody in the Spurs support was despicable, and again they succeeded in ruining the game for all decent football fans.

Jan 1, 2020: Harry Kane injures his hamstring as he scores an equalizer at Southampton which is immediately disallowed by VAR, who can’t undo the injury to Kane’s leg. Kane is out until football stops.

Southampton FC v Tottenham Hotspur - Premier League Photo by Michael Steele/Getty Images

The sadism of fate was on full display as Harry, as he loves to do, sacrificed his body to equalize in a league game. Thinks to the watchful eye of the video assistants, the goal didn’t count, meaning Spurs dropped three points. Worse yet, the team lost their attacking talisman for months, forcing Son, Bergwijn, and Lo Celso to try to fill in for him. Kane, it must be said, might benefit from the coronavirus disruption more than most, since it will force him to rehabilitate his leg instead of rushing back to play.

February 5, 2020: Jan Vertonghen’s substitution represents the end of his prime

Tottenham Hotspur v Southampton FC - FA Cup Fourth Round: Replay Photo by Chloe Knott - Danehouse/Getty Images

Anybody could have foreseen that at 32, some of Jan Vertonghen’s physical qualities will begin to decline, but nobody knew how abruptly it would happen. He struggled all season, and in the Saints FA cup tie, Vertonghen looked off the pace and unable to compete like he used to. Mourinho substituted him just after half time, and with a look of sorrow verging on tears, he walked the long way off the pitch. It was a heartbreaking moment that to many signaled the end of Super Jan’s prime.

February 8, 2020: Dele Alli posts racist coronavirus video on Snapchat

Crystal Palace v Tottenham Hotspur - Premier League Photo by Steve Bardens/Getty Images

In a season that saw a rash of racism among Tottenham’s own fans, Dele let himself and the team down when he posted a video of an Asian man with a joke about coronavirus on his social media account. He apologized for it quickly, but the sentiment was too little, too late after he tarnished the club’s reputation off the pitch.

Feb 16, 2020: Heung-min Son fractures his arm, out through football’s stoppage.

Aston Villa v Tottenham Hotspur - Premier League Photo by Simon Stacpoole/Offside/Offside via Getty Images

With Harry Kane out, the gods of luck struck down Tottenham’s next best goalscorer sometime during a 3-2 win at Aston Villa with a freak reinjury of a forearm fracture that had plagued Son earlier in his career. It seemed like nothing at first, but when he flew to South Korea to have surgery on it, fans knew something was amiss. Son gave an update a few weeks ago where he acknowledged that he had been nursing the injury throughout the Villa game but didn’t complain in order to help the team. Still no news on when he’ll be back.

March 4, 2020: Eric Dier climbs into the stands to confront a fan after Tottenham exit the FA Cup on penalties.

Tottenham Hotspur v Norwich City - FA Cup - Fifth Round - Tottenham Hotspur Stadium Photo by Tess Derry/EMPICS/PA Images via Getty Images

Losing on penalties was bad enough after 120 minutes of uninspired football from Spurs. With the Premier League out of reach and the Champions League a long shot, the FA Cup seemed Tottenham’s last real hope at a trophy. Instead, they failed to score more than once in 120 minutes against the worst side in the Premier League, and Erik Lamela, Troy Parrott, and Gedson Fernandes all missed penalties in the shootout. Then, apparently reacting to his brother being embroiled in a fracas, Eric Dier vaulted the advertising boards and sprinted up rows of stands in search of a fight. It was a bizarre confrontation that only added to the sense that something was cosmically wrong with Tottenham this season.

March 10, 2020: Tottenham wither out of the Champions League; football suspended afterward.

RB Leipzig v Tottenham Hotspur - UEFA Champions League Round of 16: Second Leg Photo by Roland Krivec/DeFodi Images via Getty Images

Without Kane, Son, or new star signing Steven Bergwijn, Spurs couldn’t find a single goal to answer Leipzig’s three. The two managers’ post-game reactions say it all: “I don’t want to say it was easy. That sounds kind of arrogant,” Leipzig manager Julian Nagelsmann mused, while Mourinho claimed that every player on Leipzig’s bench would have played in his side. The game itself wasn’t exactly bad luck—more like poor performance—but having all seasons suspended right after means that this will be the pathetic, lingering memory we have of our team.

March 31, 2020: Tottenham are the first team in the Premier League to furlough their staff.

Southampton v Tottenham Hotspur - FA Cup Fourth Round Photo by Jon Bromley/ MI News/NurPhoto via Getty Images

While other professional sports teams made headlines for their efforts to assist in the COVID-19 pandemic, Tottenham were in the news after announcing that non-playing staff would have their wages cut 20%. It was just the sort of unnecessary emphasis on the balance sheet that sums up many supporters’ contempt for ENIC, and left a sour taste in the public’s mouth amidst a global crisis. In response to pressure from players and supporters, notably a “pay the staff” tweet campaign of which many on the Carty Free masthead were a proud part, the club reversed their decision and are now converting the stadium to assist the NHS.


Who knows if or when the 2019-20 season will resume, but it’s safe to say that of all the seasons in recent memory, this was the one when everything went wrong. Not to be overly pessimistic, though: what made a lot of these moments stand out was the way that they happened right when things seemed on the verge of going right. The squad and the club still seem to be pushing in the right direction. It seems that the universe conspired to ruin this season, but against all odds, Spurs supporters still have reason to believe in the next.