Tottenham travel not to Moldova for their third Europa League fixture of the season, but to Transnistria - a sovereign state not recognised as independent by Moldova - as they take on Sheriff Tiraspol in Group K.
Spurs go into uncharted territory knowing full well that a win against their little-known opponents will put them on the cusp of qualification for the next round of the Europa League.
Manager Andre Villas-Boas has opted to leave a host of key players at home as he looks to keep his squad fresh ahead of his side's Premier League game against Hull on Sunday.
Kyle Walker, Andros Townsend and Paulinho have all been rested after their international exertions while Danny Rose, Etienne Capoue and Younes Kaboul remain sidelined.
Aaron Lennon may make his first start after picking up an injury on the first day of the season, while Emmanuel Adebayor could also feature for the first time this term.
The Portuguese boss must be wary however - Spurs slipped to a 3-0 defeat against West Ham before the international break having travelled to Russia to take on Anzhi Makhachkala three days beforehand.
Despite that Tottenham face a run of five games in 13 days, meaning the 36-year-old will likely field an under-strength team while still hoping to get the win that will help them wrap up qualification as quickly as possible.
Jermain Defoe will become Tottenham's joint-leading European scorer if he finds the back of the net tonight, putting him level with club legend Martin Chivers on 22.
Predicted Tottenham line-up to face Sheriff Tiraspol: Hugo Lloris, Jan Vertonghen, Kyle Naughton, Vlad Chiriches, Michael Dawson, Sandro, Mousa Dembele, Erik Lamela, Aaron Lennon, Lewis Holtby, Jermain Defoe