Many of the familiar names that have worn the Tottenham shirt in recent years have walked out of the exit door to leave a very new team at the club.
Spurs have had four different head coaches in a little over a year and the player turnover in the past two years had been remarkable with 29 players, who have been involved in and around the first team, heading out of the club. Ben Davies remains the longest serving player at the north London outfit and it is more than 12 years since he signed his first contract with the club.
The experienced Welshman is the only remaining member of the squad from the Champions League final in 2019 still remaining in N17.
It's time to take a look at how those 29 players who have left the club permanently in the past two years have got on after heading out of the Hotspur Way doors. A number were star names, one a Spurs legend, another the man who scored the goal that won the club its first trophy in 17 years, some were very expensive flops, while others were long-serving servants.
We are not including those who have left on loan with obligations to buy as they will not permanently leave the club until next summer.
Let's dive into the rest though and first the busy recent summer window before working our way back:
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Cristian Romero
After years of being linked with Atletico Madrid and Diego Simeone seeming to flirt with him every summer, Romero did finally head to the Spanish capital.
The La Liga side got him eventually for a cut price £34.2million package and the 28-year-old has started the past four matches after being phased into the team following his post-World Cup final rest.
Romero was recently caught up in an exchange with Jude Bellingham after a trademark aggressive tackle on the England midfielder during the Madrid derby. Despite calls for a red card, the former Tottenham captain kept his place on the pitch and in the end was left celebrating a victory for the hosts at the Metropolitano.
Djed Spence
Djed Spence wanted to leave Spurs to be a first choice right-back and he got his wish with a £30million move to Inter in the summer.
'Physical issues', according to the Italian media have held up his debut for the Italian club and he was finally expected to start full training in Milan with the other non-international players this week after being left out of Thomas Tuchel's England squad.
The 26-year-old World Cup star could finally make his debut on October 10 when Inter host Parma in Serie A or when they welcome Club Brugge in the Champions League three days later.
With Pedro Porro out with a hamstring injury, Roberto De Zerbi would have loved to have called upon Spence in recent weeks but he would not have been available either anyway.
Luka Vuskovic
Sold for £50million to Brighton in the summer as he did not want to remain a youth player out on loan, Luka Vuskovic has quickly shown Tottenham what they are missing.
The 19-year-old, deemed not ready for Spurs, has started all eight matches so far for the Seagulls and only came off in one of them, the 5-0 victory at Coventry. The teenager has already picked up a goal and an assist for Brighton and helped the team keep five clean sheets in those opening five games.
Vuskovic earned plenty of plaudits for his performance against Arsenal before the international break in a 3-0 win which sent Brighton into third place in the early table.
Tottenham hold a 20 per cent sell-on clause on any profit the Seagulls make if they sell the teenager in the coming years and have matching rights on any bid, should they want to bring the defender back to north London and he wants to return.
Yves Bissouma
Yves Bissouma left Tottenham in the summer after four years at the club when the decision was made not to take up the option to extend his contract by its final year.
The 30-year-old spent much of the summer seeming to be more concerned with the launch of a new fragrance but three months after leaving Spurs put pen to paper on a one-year contract to play for Ajax in the Eredivisie.
Bissouma played 111 times for Tottenham, scoring twice, and will be looking to make his debut in the Netherlands next month.
Joao Palhinha
Joao Palhinha made a big impression for Spurs during his season on loan from Bayern Munich, scoring seven goals and providing three assists, with some crucial strikes that helped keep the club in the Premier League.
De Zerbi was keen to keep the 31-year-old but with the £185million arrival of Mateus Fernandes and Sandro Tonali as well as the need to develop Lucas Bergvall and Archie Gray, along with Rodrigo Bentancur's presence, there was no room left at the inn for Palhinha.
The midfielder had wanted to come back to Spurs but eventually returned to Portugal with a transfer to Benfica for around £16million and has played five league games so far and helped Benfica win 2-0 at AC Milan in the Europa League this month.
Randal Kolo Muani
While Palhinha would have been a popular permanent signing, there was never any real chance of Randal Kolo Muani signing on for a longer stint in north London.
The 27-year-old scored just one Premier League goal in 30 appearances although he fared better in the Champions LEague for the club. Now he has made the move to the club he actually wanted to join last summer as Juventus agreed a deal with PSG for the Frenchman.
He has been joined by Spurs team-mates Guglielmo Vicario and Pape Matar Sarr, both on loan in Turin, and the striker has continued that patchy form for the Old Lady, without a goal in five Serie A matches but a goal and assist in his one Europa League game.
Will Lankshear
Will Lankshear, like Vuskovic, has already shown the decision to sell him this summer to Middlesbrough for £10million plus another £10million in add-ons, looks a bit daft.
At a times when Tottenham's attackers can't buy a goal, the 21-year-old has scored six of them in his first eight Championship games gamed and hit two goals in his three Carabao Cup matches. The striker also netted on his England U21s debut on Friday to continue his hot streak.
As with Vuskovic, Spurs have a 20 per cent sell-on clause, plus matching rights on any future bid for the striker.
Ashley Phillips
Also heading to Middlesbrough in the summer was Ashley Phillips. The 21-year-old moved for £7million with another potential £13million in add-ons.
The centre-back was a Spurs player for three years but never played a competitive match for the north London outfit, being sent out on loan to Plymouth and Stoke, where he spent two spells. Phillips was nominated for the Championship Young Player of the Season award in his last campaign.
The young defender is starting matches for Boro and has already got seven appearances under his belt so far, scoring his first goal for the club in the 4-3 home win against Norwich.
Manor Solomon
Manor Solomon also spent three years at Tottenham but appeared in only six competitive matches for the club before departing for West Ham this summer.
The 27-year-old was shipped out on loans to Leeds, Villarreal and Fiorentina before moving across London to the Hammers for a fee that could reach £7million.
The Israel international has already racked up 10 appearances for Nuno Espirito Santo's side, with four goal involvements in eight matches in the Championship.
Alfie Devine
Tottenham's youngest ever goalscorer, Alfie Devine made his loan season at Preston a more permanent affair after North End triggered the £6million option to sign him in the summer.
Now 22, Devine made just two appearances for Spurs but is a firm favourite at Preston where the midfielder has already made 10 appearances this season to make it 58 appearances for Preston in just over a year.
Dane Scarlett
Another 22-year-old to have made the move from Spurs this summer was Dane Scarlett, who joined Leyton Orient.
The striker came through the club's academy after joining as a child and made 27 appearances for Tottenham. His one goal came in the Europa League victory against Elfsborg on the way to the club lifting the trophy.
Scarlett was tipped for the top by the likes of Jose Mourinho and Antonio Conte and will now look to get his career going in League One with Orient. He is yet to start a match for his new side but has made four appearances so far.
Brennan Johnson
Brennan Johnson, just over six months after scoring Tottenham's winning goal in the Europa League final, was informed that he was no longer required at the club as he did not fit into Thomas Frank's plans.
A £35million move to Crystal Palace came in January and the Wales international never really fitted into Oliver Glasner's set-up.
The 25-year-old played 26 times for the Eagles and did not score, with just two assists to his name. A move to Everton came this summer in a swap deal essentially for Dwight McNeil.
Johnson is already off the mark for the Toffees, with a goal and assist in the Carabao Cup win at Preston, although he is awaiting his first Premier League goal for David Moyes' side after five appearances.
Son Heung-min
Son Heung-min left Tottenham Hotspur as a legend following a decade of service to the north London club, having scored 173 goals and registered 101 assists in 454 appearances. He became the first Asian player to net 100 goals in the Premier League and last year the South Korean star managed to do what so few before him had managed at Spurs in lifting a European trophy as captain of the club.
The now 34-year-old told Thomas Frank that he wanted a new challenge last summer and duly joined LAFC in an MLS record fee of more than £20million.
Son has revelled in the USA and has netted 20 goals and provided 23 assists in 49 appearances for the Los Angeles outfit.
Bryan Gil
Bryan Gil left Spurs last year after four years as a Spurs player but with only 43 appearances and two assists to his name. The Spaniard just never found a place in N17 and was loaned out three times over those years.
He enjoyed his final loan spell at Girona and joined the La Liga club permanently for 10million Euros (£8.7million) at the very last moments of deadline day in the summer of 2025.
The 25-year-old made 30 appearances for them last season, without a goal to his name but three assists as Girona were relegated from La Liga. Gil remained with the club and had made five appearances so far in La Liga 2 without any goal involvements.
Sergio Reguilon
Another Spaniard who exited Spurs last summer, Reguilon left at the end of his contract, having made 73 appearances for Spurs, scoring twice and contributing nine assists over his five years at the club since joining from Real Madrid. That half a decade included an ill-fated loan to Atletico Madrid and more successful half-season spells at both Manchester United and Brentford with Thomas Frank.
In his final season Spurs could not find a move for Reguilon and he ended up playing six times for the club under Ange Postecoglou when needed.
Nowadays the 29-year-old is playing with Lionel Messi at Inter Miami in the MLS after recovering from an injury-hit first half of the campaign has made 18 appearances, scoring once.
Timo Werner
Completing the hat-trick of Tottenham departures to the MLS, Timo Werner spent two loan spells at Spurs and was on the end of plenty of criticism from the supporters. He played 41 times for the north London club, scoring three goals and providing seven assists.
After returning to RB Leipzig, the 30-year-old German is now playing for San Jose Earthquakes and has six goals and five assists from 15 MLS matches this season around various injuries.
Fraser Forster
The 37-year-old played 34 times for Tottenham over his three seasons at the club and managed eight clean sheets but conceded 54 goals during those games. He made four appearances in the Europa League last season meaning he got a winners' medal after the final in Bilbao.
After a little spell without a club, Forster, an England international with six caps and plenty of experience, moved to Bournemouth in the last winter window and signed a new one-year deal in the summer.
Alfie Whiteman
The long-serving Tottenham academy product departed the club last summer after a decade in Spurs colours.
Whiteman made his competitive first team debut in a Europa League win over Ludogorets at the Tottenham Hotspur Stadium in November 2020 and had two separate loan spells at Swedish top-flight side Degerfors IF in 2021 and 2022, helping them avoid relegation from the Allsvenskan on both occasions.
The 27-year-old goalkeeper announced his retirement from football at the end of last year to move into the world of photography and directing, making a well-received video about the club's fans. He has also taken acting lessons so perhaps we'll see him on the big screen in years to come.
Pierre-Emile Hojbjerg
It feels like Hojbjerg left Spurs a long time ago, although technically he was only on loan at Marseille, playing under Roberto De Zerbi, until his contract ended at the north London club last year as he joined the Ligue 1 outfit with an obligation to buy that could rise to £17million.
The 31-year-old joined Tottenham in 2020 and played 184 times, scoring 10 goals and providing 17 assists during his four seasons before that loan to France.
Last season the Danish midfielder turned out 43 times for Marseille, scoring five goals and supplying five assists. He captained the Ligue 1 side for much of the season. This season he has played every minutes so far for the Ligue 1 outfit, scoring in the opening day win against Strasbourg.
Tanguy Ndombele
Tanguy Ndombele will be remembered as Tottenham's biggest flop after arriving from Lyon for a club record fee worth more than £60million back in 2019.
The Frenchman played just 91 times though over half a decade at the north London outfit before having his contract mutually terminated in the summer of 2024.
He moved back home when Nice signed him on a two-year contract. It was all going reasonably well to begin with before injuries galore wrecked his time there.
Last season he did not make his first appearance until December. He would go on to play just eight league games, with only 272 minutes on the pitch in those games, starting just one of them.
When his contract came to a close at the end of June, Ndombele became a free agent. The problem for him as that, as of this point, no club has rolled the dice on the midfielder, who will turn 30 in December.
There have been some links with Marseille, where his old Lyon boss Bruno Genesio currently coaches although the 60-year-old's position is said by the French media to be under threat.
Ndombele's last permanent social media post came just two days before his contract ended at Nice. With the caption "Just chilling", it featured a collection of images of him on holiday, playing five-a-side indoor football, working in the gym and some training ground videos. All eyes are on what he does next.
Giovani Lo Celso
Another expensive signing in that summer of 2019, Giovani Lo Celso had injuries aplenty at Tottenham and played 108 games for the club, scoring 10 goals and laying on eight assists.
Those injury woes followed him to Real Betis and the Argentine, now 30-years-old, played 32 games with three goals and three assists around a hamstring injury last season. He has made just the one appearance so far during this campaign.
Emerson Royal
Emerson Royal is back in Brazil with Flamengo after a difficult time in Italy with AC Milan immediately after leaving Spurs in 2024.
The 27-year-old right-back left Tottenham in a deal worth £12.6million plus add-ons but Emerson struggled to impress in Serie A, although he did win the Italian Super Cup.
Emerson has found himself in and out of Flamengo's league side this season but has been getting some cup games, and has made 49 appearances in all for the Brazilian side.
Troy Parrott
Troy Parrott is one of the biggest success stories among the Tottenham exits in recent years. He has already scored a late winner for new side Betis against Real Madrid and then netted another winner on his Champions League debut away at Lille.
The 24-year-old Republic of Ireland international netted Spurs around 4million euros thanks to the 20 per cent sell-on clause when he moved to Spain from AZ.
Parrott hit 51 goals and supplied 17 assists in 97 appearances for the Dutch side. He also has 12 goals now for his country after really kicking on in his development.
Ryan Sessegnon
Everyone just wanted to see Ryan Sessegnon playing football again after years of hamstring injury hell at Spurs and he's rebuilt his career back at Fulham.
Now 26, the left-back played 31 times last season as a near ever-present for Marco Silva, with three goals and three assists, and this campaign under new boss Alvaro Arbeloa he has come of the bench three times in the Premier League and started in the 3-0 Carabao Cup win with an assist at AFC Wimbledon.
When Tottenham decided not to take up the option of the additional year on his contract in 2024, Sessegnon's return to Fulham meant that all of the club's arrivals in that now infamous 2019 window, including Ndombele, Lo Celso and even Jack Clarke went back to their previous side at some point after joining Spurs.
Joe Rodon
Joe Rodon has not looked back after leaving Tottenham as he helped Leeds United to the Championship title and missed only four minutes of football in their entire promotion-winning league season before impressing in the Premier League.
Since joining permanently as part of the deal that brought Archie Gray in the opposite direction to north London that summer, now the 28-year-old has played 139 times for United.
He was starting regularly again this season under Daniel Farke until a hamstring injury last month ended that run.
Oliver Skipp
Oliver Skipp is now at Charlton on a season-long loan deal from Leicester City as the Addicks' 11th and final signing of a busy summer transfer window.
The 26-year-old suffered two relegations with the Foxes, making 68 appearances for them before his switch to Championship side Charlton this month.
Skipp had left Spurs in 2024 after 18 years at the north London club and more than 100 first team appearances in a transfer that could eventually bring Tottenham more than £20million plus an eventual sell-on clause.
Japhet Tanganga
Like Sessegnon, Japhet Tanganga left Tottenham and in doing so left his injury woes behind.
Tanganga, now 27, signed on a free transfer for Millwall after impressing for the Championship side on loan last season and then last year made the move to Sheffield United and he captained the Blades as he continues to develop in his career.
This season he has played every minutes, apart from being rest for one Carabao Cup matches, with 10 appearances and one goal against Bolton this month.
Ivan Perisic
It feels like the Croatian left a long, long time ago, but Ivan Perisic technically stopped being a Tottenham employee in the summer of 2024, even if he had already joined Hajduk Split the previous January on loan until the end of his contract.
His time at Spurs ended with that torn cruciate ligament and then his return to Croatia with Hajduk went in the wrong direction with the arrival of Gennaro Gattuso as the now 37-year-old's contract was mutually terminated.
That brought a move to another new league in his remarkable career with a switch to Dutch side PSV Eindhoven and age has been no barrier for Perisic as he has racked up a remarkable 28 goals and 28 assists in 87 matches for the Eredivisie side.
Eric Dier
Similar to Perisic, Eric Dier has been gone from Spurs for longer but only officially left in that summer of 2024 after the option in his loan move to Bayern Munich was triggered in the second half of that season.
In all Dier played 48 matches at Bayern and left as a title winner for a new chapter at Monaco, where he signed a three-year contract.
The 32-year-old has been drawing plaudits for his performances in playing every minute this season for the Ligue 1 side, where he has also been going through his coaching development with the academy.