Thomas Frank will visit the Parc des Princes in a rematch against Paris Saint-Germain in his first UEFA Champions League campaign as a head coach.
The Dane's first competitive match in charge at Tottenham was the UEFA Super Cup final, where a gallant performance was eventually undone by a penalty shootout defeat to the Parisians.
Spurs qualified for this season's competition as UEFA Europa League winners, having beaten Manchester United 1-0 back in May, and will play two sides they met on their journey to glory.
It is an away trip to Germany to take on Eintracht Frankfurt and another trek to the frozen north of Scandinavia to meet Bodø/Glimt again.
There are more than just familiar faces, however, as debut European outings against FC Copenhagen and Villarreal were also generated.
Tottenham have met the remaining three teams before in Europe. Borussia Dortmund and AS Monaco have provided some memorable and not so memorable experiences for Spurs fans in the last decade.
Spurs have a 100% win record against the Black and Yellows in four Champions League matches. It is a different story against the Monegasques, however, having lost both encounters in 2016/17.
In fact, of the eight teams drawn, Monaco - now home to former defender Eric Dier - are the only ones to have beaten Tottenham in the Champions League.
Slavia Prague, meanwhile, were narrowly dispatched by Juande Ramos' side over two legs in the 2007/08 UEFA Cup.
Tottenham Champions League opponents
Paris Saint-Germain (a)
Borussia Dortmund (H)
Eintracht Frankfurt (a)
Villarreal (H)
Bodø/Glimt (a)
Slavia Prague (H)
AS Monaco (a)
Copenhagen (H)
*Full dates and match times will be released by UEFA on Saturday.
Frank's adaptability key to success
Although it is very much the early days of Frank's Tottenham career, he has exhibited a tactical flexibility that could be perfect for European tournaments.
The Super Cup final saw him deploy a back three system with Kevin Danso joining Micky van de Ven and Cristian Romero, which did a superb job of congesting the defensive third and marshalling much of PSG's attacking threat - for 85 minutes.
But the recent 2-0 win over Manchester City further showed Frank's nous. Many expected him to revert to the back three/wing-back formation after a more conventional 4-3-3 against Burnley.
He instead continued with that convention, asking van de Ven and Romero to not give City's forwards a moments peace. Even if that meant following them deep into the attacking third.
It is the kind of bravery and aggression that Spurs so often lacked at the end of Ange Postecoglou's tenure. Though the Europa League journey the Australian lead did showcase one aspect of the squad that Frank has yet to experience - seeing games through while being under the cosh.
Nevertheless, it is only three matches in for the former Brentford manager and he is able to count on a squad that have progressed through continental matchups in that fashion before.
Ultimately, Frank wants Tottenham to be an attacking outfit, and the eight fixtures ahead should provide him ample opportunity to put that into practice as well. Namely in the ties against Copenhagen, Slavia Prague and Bodø/Glimt.
The precarious nature of the new format means that bold approaches may hold more power, given the number of wins and goal difference were vital to many teams' fortunes last year.
Dinamo Zagreb and VfB Stuttgart, for example, left the competition at the first hurdle last season despite both winning three matches.
It may seem straightforward to aim to win as many games as possible, but in the Europa League, with its generally weaker calibre of opposition, meant Spurs could not shy away from that.
This time round, against more consistently stronger sides, being tactful will be crucial to sealing a place in the knockout stages, and Frank looks primed to deliver that.