Five... players to play for Spurs and Milan

As we prepare to step into the San Siro for our UEFA Champions League Round of 16, first leg against Milan on Tuesday evening (8pm UK), here are five players to have pulled on our famous lilywhite shirt and I Rossoneri's red and black stripes, starting with a certain Jimmy Greaves...

Jimmy Greaves

14 appearances/nine goals for Milan, 1961; 379 appearances/266 goals for Spurs, 1961-70

Jimmy Greaves joined Milan from Chelsea in June, 1961, but had returned to London and Spurs by the end of the year in a £99,999 deal. Naturally, Greavsie scored on his Serie A debut against Vicenza, but his time was short lived in Italy, and Bill Nicholson got his man during December, quite an addition to his double-winning squad of 1960/61.

Of course, Jimmy delivered again on his debut, this time in spectacular style with a hat-trick in a 5-2 win against Blackpool and later scored in the final against Burnley as we retained the FA Cup. He would add the European Cup Winners' Cup medal in 1963 and another FA Cup in 1967 before moving to West Ham in 1970, having scored a Club record 266 goals in 379 appearances - a record that stood for 53 years until Harry Kane reached the magic 267 against City on 5 February.

Carlo Cudicini

Three appearances for Milan, 1991-93; 37 appearances for Spurs, 2009-12

Following in his father Fabio's footsteps, Carlo Cudicini progressed through the youth set-up at Milan to make his only two appearances in the Champions League, against Porto in March, 1993 and PSV in April, 1993. He then played for Como, Prato, Lazio and Castel di Sangro before joining Chelsea in August, 1999.

He made over 200 appearances for the Blues between 1999-2009, the majority between 2000-2004. At the end of the 2002/03 season, Carlo won the Premier League’s Golden Gloves award for goalkeeper of the year and during his time at Chelsea he twice picked up winner’s medals in the Premier League, FA Cup, League Cup and Community Shield. Carlo joined us in 2009 and made 37 appearances before a switch to LA Galaxy. He's now a loan player technical coach at Chelsea.

Edgar Davids

29 appearances/2 goals for Milan, 1996-98; 44 appearances/1 goal for Spurs, 2005-2006

Edgar Davids joined AC Milan from Ajax during July, 1996 and played just 29 times for I Rossoneri before moving to Juventus in December, 1997. He had spells at Inter and Barcelona before joining us in August, 2005. He made 44 appearances for us before returning to Ajax in January, 2007. Edgar returned to England for a brief spell at Palace in 2010 and was then player-manager at Barnet between 2012-2014. He was part of Holland's coaching team at the 2022 World Cup in Qatar. Capped 74 times by Holland, he won three Dutch titles, the UEFA Cup and the Champions League with Ajax and later three Serie A titles with Juve.

Christian Ziege

47 appearances/4 goals for Milan, 1997-99; 55 appearances/10 goals for Spurs, 2001-04

After seven years, two Bundesliga titles and a UEFA Cup win in 1996, followed by Euro 96 success with Germany, Christian swapped home for Italy and Milan, where he added to his medal haul with a Serie A title in 1998/99. He moved to England and had spells at Middlesbrough and Liverpool, helping the Reds to a cup treble (League Cup, FA Cup, UEFA Cup) before joining us in July, 2001.

Possessing a wand of a left foot, Christian scored in the 2002 League Cup Final loss to Blackburn, became the first Spur to play in a World Cup Final when Germany lost out to Brazil in 2002, then scored a memorable free-kick against Arsenal in December, 2002, but then suffered a serious thigh injury that almost ended his career. He eventually returned to Germany and Borussia Monchengladbach in 2004, retired in 2005 and has taken up a number of coaching roles, his latest at Austrian side FC Pinzgau Saaldelen.

Kevin-Prince Boateng

24 appearances for Spurs, 2007-09; 114 appearances/8 goals for Milan, 2010-16

Berlin born, 'The Prince' progressed through the Hertha BSC youth scheme to score five goals in 54 senior games until joining us during July, 2007. He made his senior debut on our UEFA Cup visit to Anorthosis on 4 October and went on to make 24 league and cup appearances. He had a loan stint with Borussia Dortmund between January and May, 2009 and moved on to Portsmouth at the end of August, 2009. He moved from Pompey to Genoa and onto Milan in 2010.

He landed a Serie A title in 2010/11 and after a spell at Schalke, returned to Milan in 2015/16. From there, the midfielder played for Las Palmas, Eintracht Frankfurt and Sassuolo before helping Barcelona take the La Liga title on loan in 2018/19. He's since turned out for Fiorentina, Besiktas and Monza, and is now back in Germany at Hertha Berlin.