It has been over five years since Tottenham Hotspur stepped out on the greatest stage in European club football.
The 2019 Champions League final may have ended in defeat, but it was a seminal moment in the modern history of the Lilywhites nonetheless. The idealised aftermath would have been building on such an achievement. As it has come to pass, Spurs have not progressed further than the round of sixteen in continental competitions since.
After a year absent from all European ventures, Tottenham are back in the Europa League with renewed hope of a cup run, buoyed by a fresh format and Ange Postecoglou’s recounted second season success.
History has been much kinder to Tottenham in the Europa League than recent times, with the club winning the inaugural UEFA Cup in 1972 and finishing runners-up two years later before collecting another of the handleless trophies in 1984.
In the 21st century, the quarter-finals have been the apex of Spurs success in Europe’s secondary prize. The lowest point was perhaps the very last outing – a 3-0 loss to Dinamo Zagreb as the Croatian side toppled Tottenham’s 2-0 home victory.
That was just over three years ago and a lot has changed in North London since. But with the final back in Spain, - in the city of Bilbao - can Spurs change their fortunes and usher in another coveted final?
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Fixtures and opponents
Tottenham begin their Europa League campaign at home to Qarabag FK, the champions of Azerbaijan and the side in which Heung-min Son scored his first two goals for Spurs against back in 2015.
It is one of four home matches in UEFA's revamped league phase format, with the Lilywhites also hosting AZ Alkmaar, Roma and IF Elfsborg.
On the road, Tottenham have some pretty tricky tests and hostile atmospheres. Ferencvaros, Rangers, Galatasaray and Hoffenheim all welcome Postecoglou's side, with the former Celtic boss in particular unlikely to receive the warmest of receptions when returning to Ibrox.
If European glory is the aim then this run of eight fixtures will certainly provide enough variety to check Spurs' credentials.
Perhaps the stiffest matchup will be the visit to Galatasaray. After a glittering playing career, Okan Buruk has captured two consecutive league titles for the Yellow Reds with a press-hungry, attack-minded side who focus on width - sound familiar?
Spurs will probably be met with this kind of aggression in all their away games. Not simply because they all have notoriously passionate support, but because they all have coaches who pride themselves in high-pressing.
This could work to Postecoglou's advantage since Spurs have a higher calibre of player and could potentially beat the likes of Ferencvaros, Rangers and Hoffenheim at their own game.
With Victor Osimhen now alongside Dries Mertens, Lucas Torreira and a certain Davinson Sanchez, Galatasaray have the talent to confront Spurs more in this regard. Though in a similar vein, are susceptible on the counter.
Back at N17 Tottenham will be able to be as assertive as they have been in the opening five Premier League games.
Under new coach Ivan Juric, Roma will be more defensively-minded than Daniele De Rossi's tenure while AZ's on the front foot style is led by Spurs academy graduate Troy Parrott. Elfsborg, meanwhile, will have adjusted to life after Jimmy Thelin by the time they visit England in late January.
Though with 24 of the initial 36 teams going through to the knockout phase, it would be difficult to foresee Tottenham not reaching the next stage of the competition.
But with a possible seventeen extra fixtures on the board should Tottenham land in Bilbao in May, a fresh squad will be integral.
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Squad strength
The most notable aspect of Postecoglou's squad selection earlier this month was the omission of Djed Spence and Sergio Reguilon.
Due to UEFA rules which state teams must have four club-trained players, Spurs were deducted two squad slots due to only having Brandon Austin and Alfie Whiteman fitting that bill.
Clubs must also have eight homegrown players, meaning the last spot in the twenty-three-man squad was between Fraser Forster and Spence, with the goalkeeper being chosen in the end.
This does mean Tottenham have lost versatile options in the full-back area. Given the importance of the position in this current system and the risk of overplaying Destiny Udogie and Pedro Porro, Spence and Reguilon will have to target the Carabao Cup and Premier League cameos.
Teams are able to make amends to the squads in February ahead of the knockout phase, but, until then, Archie Gray and Ben Davies will have to play understudy, as well as fill in at midfielder and central defence respectively.
Teenagers Wilson Odobert and Lucas Bergvall offer their sprightly talents on the wing and in the middle. Though they have not been too far from the first-team picture already this season, there will be more of an opportunity for starting places despite the strong opposition in the league phase.
The return of Richarlison will also be invaluable. As Dominic Solanke continues to settle into the swing of things, the Brazilian's energy and fox-in-the-box presence will give an extra dimension to the forward line.
It is also worth noting that Rodrigo Bentancur's twelve-match FA ban will not apply in European football. The Uruguayan will almost certainly be a starter for every Europa League match until December.
European campaigns are often a careful balance between rotation and strength - something Postecoglou did not have to contend with much during his first year at the Tottenham Hotspur Stadium.
It will be a new challenge for the 59-year-old, whose tweaks to the line-up are often limited to one-or-two alterations in midfield and attack bar enforced absences.
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Chances of winning
It has been sixteen years since Tottenham's last trophy and the fan base is famished of silverware.
Even after one year on the job, Postecoglou is similarly hungry for honours, "I failed last year in my head because that's how I'm geared. I think I've made it pretty clear what my expectations are.
"But that doesn't mean that I stop. That just fuels a fire. 'Why didn't I do it?', 'why didn't I achieve last year?'."
This Europa League will be, like all other elite football competitions, very difficult to win. The likes of Manchester United, Athletic Bilbao, Porto and Jose Mourinho's Fenerbahce are just some of the names that will provide stern competition for the Europa League crown.
Thus far this campaign Spurs have largely dominated games in terms of possession and shots taken, although the xG metrics and actual accumulated goals tell a story of finishing frustrations.
A scraped win against Coventry and a positive display in the 3-1 victory over Brentford have been potential turning points in a start to the season that has delivered what performances have warranted.
Should Tottenham reach the knockouts, Postecoglou will also have to navigate the task of two-legged ties - another aspect he has not yet encountered since taking over.
This is likely where his "we never stop" mantra will be scrutinised most intensely as in-game management becomes even more crucial.
Knitting together a solid run in the Europa League would be a major boost to the Postecoglou project. Before a Europa ball has been kicked, Tottenham are currently odds on favourites to lift the trophy - an achievement that would catapult Postecoglou into hero status among the Lilywhite faithful and immediately slot into Daniel Levy's top three.
Based on the strongest elevens, Tottenham are well among the most capable teams in the competition. And, in contrast to previous years, the discrepancy between the first choice line-up and the substitutes bench is gradually narrowing.
However, the showings of deputies such as Radu Dragusin, Timo Werner and Gray will be all the more vital given the higher turnover of important matches.
The trophy question will loom over Spurs until it is sufficiently answered. Though in the five-season continental malaise since the Champions League final, going beyond the quarter-finals will feel like a step in the right direction.
Although not for Postecoglou, as basking in Basque Country-set glory is the only aim.
"If I came out and said 'yeah this [creating a winning team] is going to take three or four years then it would relieve pressure. But I don't want to wait three or four years. This year's an opportunity."
