(credit: UEFA Official vs YouTube/ imago)
(credit: UEFA Official vs YouTube/ imago)

Tottenham's best-ever deadline day signings: Robbie Keane and £47m hero

Kyrenia Shipillis

Kyrenia is a lifelong Tottenham fan who has been writing for Tottenham News since she joined Breaking Media in 2025. She will graduate with a Master's in Sports Journalism from St Mary's University, Twickenham in 2025. She spent several months working for the Non-League Paper and has written for the Sports Gazette. Her earliest memory of the Lilywhites is sitting alone in her dad's room in front of the telly crying into her bowl of popcorn as she watched as her team were thrashed...yet again. She is happy to report that fonder memories have since blossomed.

Published on

Tottenham have struck some absolute bargains on deadline day over the years.

It is that time of year again when Premier League clubs frantically attempt to wrap up transfers which should have been done weeks in advance.

Tottenham are not excluded from this group. Indeed, Spurs have had their fair share of exceptional deadline day signings in the past, as Tottenham News takes a look down memory lane.

Daniel Levy Tottenham
Levy has overseen several strong signings while at Tottenham (Credit: Imago)

Hugo Lloris

Tottenham signed Hugo Lloris from Lyon for a reported fee of £12million on 31 August 2012.

Lloris became one of greatest captains in Tottenham's history before leaving the club in December 2023.

  • Lloris' debut for Spurs came in September 2012 against Lazio in the UEFA Europa League
  • Tottenham's best-ever defensive record came when Lloris was at the helm. During the 2016/17 season, the Lilywhites conceded only 36 goals

With almost 450 appearances for the North London club, his final game was a 6-1 defeat to Newcastle United in April 2023. Son Heung-min reunited with Lloris at LAFC in August 2025.

Los Angeles FC goalkeeper Hugo Lloris looks unhappy
Lloris became a legend at Tottenham (Credit: Imago)

Robbie Keane

Tottenham agreed a £7million fee to sign Robbie Keane from Leeds United on 31 August 2002.

While the Lilywhites finished in a disappointing 10th place that season, Keane was the highlight of the season.

  • Keane's 14 goals helped Spurs avoid relegation during the 2003/04 season
  • The forward won Player of Year three times during his Tottenham career, becoming the first player to do so
  • Keane was also the first player to score double figures in the Premier League in six consecutive seasons

Despite signing for Liverpool in the summer of 2008, Keane rejoined Tottenham at the end of the winter window on 2 February 2009.

Rafael van der Vaart

Tottenham signed Rafael van der Vaart on 31 August 2010 from Real Madrid, two hours before the window closed.

Spurs supporters underwent an antagonising wait at the time as problems with the computer servers meant that the necessary paperwork was not completed on time. But the Premier League granted the North London club a special dispensation and van der Vaart became a Lilywhite.

  • van der Vaart ended his first season as Spurs top goalscorer in the Premier League, scoring 13 goals
  • During the 2011/12 season, he equalised Robbie Keane and Teddy Sherinham's record by scoring in five consecutive Premier League matches

Van de Vaart's time in North London was short and he returned to his former club, Hamburger SV on 31 August 2012.

Brennan Johnson

This fee saw Johnson become one of the Lilywhites most expensive signings at the time.

  • Johnson ended the 2024/25 season as Spurs' top scorer with 18 goals
  • His first game was during an away defeat to Wolves in November 2023

While he has been criticised at Tottenham in the past, Johnson's match-winner won Spurs the UEFA Europa League trophy during the 2024/25 season.

Brennan Johnson in the new Tottenham kit staring forward
Johnson helped Spurs lift their first trophy in 17 years (Credit: Imago)

Lucas Moura

Lucas Moura signed for Tottenham on 31 January 2018 from PSG for a transfer fee of around £25m.

Moura is best remebered at Spurs for scoring a second half hat-trick in Spurs 3-2 victory over Ajax in the second left of the UEFA Champions League semi-finals.

  • Moura scored his first goal in his first start in the FA Cup tie against Rochdale on 18 February 2018
  • His final goal for Tottenahm came during a 4-1 win over Leeds on 28 May 2023

In August 2023, Moura returned to Sao Paulo after three months without a club.

Sign up for the daily Tottenham News newsletter on Substack and our new WhatsApp channel to have all the latest, breaking Tottenham Hotspur news sent straight to your phone.

www.tottenhamhotspurnews.com