European football has a habit of throwing up weird and wonderful trips, with Spurs' Europa League campaign this year taking them from Tbilisi to Tromso, via Moscow and, most interestingly, Tiraspol.
The city lies 43 miles east of Moldova's capital Chisinau and would be the second biggest city in the country was it not the capital of the breakaway state of Transnistria.
Following the dissolution of the USSR, the region declared independence in 1990, leading to a civil war that ran until a ceasefire was reached two years later.
Transnistria now has its own passports, currency, police, army and border guards - yet, to all intents and purposes, it is considered part of Moldova.
Its parliament is not recognised by any other government and the 2,216 square mile strip of land is now one of the world's last surviving communist outposts.
Soviet hallmarks pepper the landscape, with monuments of Lenin complemented by hammer and sickle emblems everywhere you go.
It leads to a rather surreal experience, confused further by Sheriff's domination of the Moldovan top flight.
Only formed in 1996, the team have won the national title 11 times since 2000 and are on course to do so again this season.
It is a confusing identity for a club that dominates the fiercely independent Transnistrian capital, where Moldovan Independence Day is boycotted.
"For this moment, we consider ourselves to be the main force in Moldova in terms of football," Sheriff manager Veaceslav Rusnac said.
"Our results speak for us because in the last years we almost always become champions and every time we are in European competition it helps us.
"Probably there are areas in Europe that think we have a lot of vodka and bears, but it is not so.
"In terms of football and working in football, there are not too many places in the former USSR that have such conditions."
Rusnac is right, Sheriff boast an incredible complex.
Built at a reported cost of £123million, the facility on the outskirts of Tiraspol includes the 13,000-seater Stadionul Sheriff, a smaller 8,000 capacity stadium, an indoor hall holding 3,500 and a five-star hotel.
It is a fine complex but one that only highlights the stark divide between rich and poor in a state no-one knows.