We look at eight current and former players to represent Tottenham and Ajax – and whether they can be considered successes at each club.
Tottenham against Ajax is not a Champions League semi-final many will have predicted at the start of the season, but it is a welcome tie for those with allegiances to both teams.
There are four members of the current Spurs squad who once donned the red and white of the Netherlands' most famous outfit, while another four represented each in some fascinating careers.
It is fair to say the majority have been successes in London and Amsterdam – provided you accept that Mauricio Pochettino not winning a trophy does not automatically make him and his team a failure – but that cannot be said for all of them.
Below, we look at eight players to cross this particular divide, and how well they did it.
TOBY ALDERWEIRELD - HIT
Alderweireld won three Eredivisie titles in a row in 2011, 2012 and 2013 after breaking into the Ajax side in 2009. He was part of a vibrant team that included future Spurs team-mates Christian Eriksen and Jan Vertonghen, and goals in European competition against AC Milan and Manchester United alerted the attention of the continent.
Atlético Madrid landed a relative bargain when they signed him in 2013 for a reported €7million fee. A loan at Southampton under Pochettino followed before he joined Spurs permanently in 2015, where he has impressed ever since.
CHRISTIAN ERIKSEN - HIT
Eriksen stood out in that Europa League tie with Manchester United seven years ago, despite being only 20 at the time. It was a sign that Ajax's exceptional young star was destined for greater things.
Ajax were disappointed to lose him to Spurs just a year later, but he is remembered warmly as a player who helped them to three league titles in a row before heading for the Premier League. Plus, when Johan Cruyff compares a 19-year-old to Brian and Michael Laudrup, you can hardly blame him for pursuing a future on one of Europe's grandest stages, where he continues to shine.
DAVINSON SANCHEZ - HIT... SO FAR
Another who impressed in a Europa League match against United – this time the 2017 final, which Ajax lost 2-0 – Sanchez spent only a year in Amsterdam after joining from Atlético Nacional.
While he was not an Ajax academy product, the centre-back nonetheless quickly embraced the Cruyffian methods at the ArenA and earned a reported £42million transfer to Spurs thanks to his player-of-the-year form.
After something of a shaky introduction to the Premier League, Sanchez has looked at home alongside his more experienced defensive partners and impressed at last year's World Cup, too. Not bad for someone yet to turn 23.
JAN VERTONGHEN - HIT
Vertonghen established a formidable partnership with Alderweireld at Ajax, after honing his skills with a loan stint at RKC Waalwijk after first breaking into first-team football.
Twice a league champion and Ajax's player of the year in 2012, he has been a key component of Spurs' rise to consistent Premier League contenders under Pochettino. Ajax fans recall him fondly as a defender of poise and composure, even though he dropped the Eredivisie trophy on his own foot – twice.
EDGAR DAVIDS - HIT AND MISS
Davids burst onto the scene with the all-conquering Ajax side who won the Champions League in 1995. A storied career in Serie A with AC Milan, Juventus and Inter followed, with a loan to Barcelona thrown into the mix.
So it was that, when he arrived at White Hart Lane in 2005, Davids' significant powers were on the wane. He only made nine league appearances in the second of his two seasons at the club before heading back to Ajax, but fans still enjoyed his time in north London.
MIDO - MISS
Mido moved to Ajax after playing for Zamalek and Gent, and it was in Netherlands that he began to catch the eye of some major European sides.
He ended up at Tottenham via Marseille and Roma, enjoying a fine season on loan in 2005-06, but his relationship with manager Martin Jol seemed to sour when he joined the club permanently and he later conceded the move was a mistake.
Mido won a second Eredivisie title with Ajax in 2011, during one of four loan moves away from Middlesbrough, who had bought him from Spurs. He ended his playing career at Barnsley.
STEVEN PIENAAR - MISS
Pienaar moved to Ajax as an 18-year-old, having developed at the Ajax Cape Town academy. He was quickly identified as a top talent and was signed by Borussia Dortmund at the age of 23, but he never really settled in Germany.
Having impressed in the Premier League for Everton, Tottenham signed him in January 2011, but injuries plagued a difficult spell in north London and he returned to Goodison Park a year later, having never quite managed to wow Spurs fans.
RAFAEL VAN DER VAART - HIT
A leading figure as a teenager in the Ajax first team, Van der Vaart moved to Tottenham via Hamburg and Real Madrid at the age of 27.
He enjoyed some of the best football of his career at White Hart Lane, becoming a real fan favourite as part of a side bursting with talent that included Luka Modric and Gareth Bale.
Trophies may have eluded him in England, but few Spurs fans consider Van der Vaart anything like a disappointment, even if they only enjoyed him for two years.