We have quite some transfer history with Tottenham, but except Zokora to some extent and I’m not sure about Dimitriescu as I was 3 years old at the time - Kanoute became a club legend and Lamela was on fire before he got injured (to be continued).
On the other hand however, most of what they’ve got from us either didn’t make sense or didn’t work out. Juande Ramos, Fazio, Gil… Reguilon is a mix (although not technically our transfer).