Is Tottenham’s 2019 summer time switch window the worst EVER?

Tottenham Hotspur played in their first ever UEFA Champions League final on June 1 in 2019.

What could have been the greatest night in the club’s history ended in disappointment as Spurs fell to a 2-0 loss to Liverpool in one of the least exciting European finals in recent memory.

However, what happened over the next few months was perhaps even more disappointing.

Spurs spent more than £100 million during that summer, plus another £60m in the following January, but ended the Premier League season sixth – 40 points behind runaway champions Liverpool.

Tanguy Ndombele and Ryan Sessegnon cost a combined sum of £90m in 2019 but are both now set to leave this summer on free transfers.

Mauricio Pochettino‘s Spurs were the ultimate ‘nearly team’ in the last decade.

As well as losing the Champions League final, Pochettino’s men fell at the last hurdle in the 2014-15 EFL Cup. Meanwhile, in the Premier League, Pochettino twice saw his team finish a season with the best goal difference – in 2015-16 and 2016-17 – but they were not crowned champions on either occasion.

There was a feeling around Spurs that they just needed to make one or two good signings to help them finally end their much-discussed trophy drought.

In the summer of 2019, signings finally arrived. But with hindsight it is now fair to declare that they were not good.

Ndombele became Tottenham’s club-record signing in July 2019 when he arrived from Lyon in a deal worth £65m.

Fast-forward five years and Spurs are now in talks with Ndombele with the aim of terminating his contract 12 months early.

Losing your most expensive signing ever on a free transfer would be bad enough but Spurs will likely have to pay Ndombele a compensation fee.

Ndombele – who has repeatedly faced criticism for failing to maintain high fitness levels – has not played for Spurs since January 2022.

The 27-year-old midfielder has been loaned out to Lyon, Napoli and Galatasaray in the past three seasons.

Meanwhile, Spurs have already confirmed that Sessegnon – a £25m signing from Fulham in 2019 – will depart when his contract expires on June 30.

The former England U21 star only managed 57 games across five injury-hit seasons in north London.

Tottenham also spent £10m on Jack Clarke from Leeds United in their dismal summer of 2019.

Winger Clarke did not make a single Premier League appearance for Spurs before leaving to join Sunderland in a cut-price move three years later.

Tottenham’s other two ‘permanent’ summer signings from 2019 – youngsters Isak Midttun Solberg and Kion Etete – are also long gone.

The last man standing is Giovani Lo Celso, who joined Spurs from Real Betis on an initial loan in August 2019 before signing for real in a £27.2m deal five months later.

Sadly, Lo Celso looks set to leave Spurs without ever fulfilling his early promise.

The 28-year-old won the Copa America with Argentina in 2021 but has only delivered three goals in 77 Premier League games for Spurs.

Lo Celso has just 12 months remaining on his contract and has been linked with a possible switch to Aston Villa in the coming weeks.

As well as signing badly in 2019, Spurs also lost England right back Kieran Trippier to Atletico Madrid for just £20m that summer. Trippier was then part of the Atletico team that won La Liga in 2021.

Manager Pochettino left Tottenham two and a half months after the transfer window closed in 2019 when he was sacked following a sluggish start to the new season.

Spurs and current manager Ange Postecoglou will be hoping for a much better summer in the transfer market in 2024.

Postecoglou is keen to recruit a new striker, while full backs and central midfielders are also high on his wish-list.