Tottenham Hotspur and the Europa League have had a turbulent relationship in recent times.

The selection of Fiorentina as their round-of-32 opponents will reinforce the mixed feelings towards playing in it that have their roots in the north London club’s recent history.

The initial return to what was still known as the UEFA Cup back in 2006 was a mostly pleasant experience for Tottenham. After only one brief run in Europe in the previous 13 years (following the 1999 League Cup success), a new generation of supporters and players at last had a chance to enjoy meetings with exotic/glamorous/strange opposition like those before them.

Martin Jol’s Spurs did not replicate the continental success of Bill Nicholson’s teams of 1963 and 1972, nor Keith Burkinshaw’s in 1984. Still, resplendent in the traditional all-white kit generally reserved for European competition, the likes of Dimitar Berbatov, Jermain Defoe and Robbie Keane lit up White Hart Lane again. The sense of ambition extended to memorable away wins over teams like Besiktas and Braga were also enjoyed.

The quarter-final exit to Sevilla was a disappointment, but the Lane rocked even in defeat. Champions League football was still longed for after successive fifth-place Premier League finishes, but European football of any kind was not to be sniffed at.

Gradually, though, things changed. As Spurs’ league form dropped off in the following two seasons, the UEFA Cup provided scant relief, and more argued, a distraction.

Harry Redknapp viewed it as much when a second-round meeting with Shakhtar Donetsk had to be negotiated in the run-up to the 2009 League Cup final. He fielded a weakened team and Spurs were knocked out.

With a cup final ahead and given they were still struggling in the league at that point, the prioritising was understandable. Yet, it established an idea of the UEFA Cup/Europa League as more work than something to enjoy, one that has only intermittently been deviated from since then.

After the memorable Champions League run of 2010-11, Redknapp‘s focus in the following campaign was getting back there. Subsequently, Spurs attacked the competition with less than their full might and fell out of the group stage.

The next two managers Andre Villas-Boas and Tim Sherwood treated it more seriously. There were memorable wins over Olympique Lyonnais, Inter Milan and Dnipro Dnipropetrovsk. But these two-legged knockout rounds also proved gruelling affairs.

Spurs’ spring struggles in the league were not directly because of their extra-curricular adventures. But the effort put into extra-time games with Inter and Basel in 2013 did not help either as Villas-Boas’ side narrowly missed out on fourth place and Champions League football. Spurs did not reach the quarter-finals last season, but the run to the last 16 stretched the squad’s resources again for sure.

All this informs the present because the prospect of playing Fiorentina is ideal, or perhaps suitable, in a couple of respects.

Tottenham’s difficulties against Besiktas in the Europa League group suggested Mauricio Pochettino’s young side might not be quite equipped for a deep run in the competition (or at least that they have plenty to improve). One which, starting with la Viola, would necessitate them beating some strong sides.

Even with a Champions League place at stake for the winners, if Spurs are not going to be good enough to win the whole thing, it would be better for them to find out sooner rather than later. It would avoid their domestic affairs suffering on account of ultimately unnecessary fatigue.

While only eighth in Serie A, Vincenzo Montella’s side possesses considerable talent which will test Pochettino’s men. Spurs would do well to overcome an experienced side that includes the firepower of Mario Gomez, the skill of Juan Cuadrado and the creativity of midfield men Alberto Aquilani and David Pizarro.

Indeed, the opposite, more positive outlook to this draw is Fiorentina might just be the opponents to spark Spurs into life in the Europa League this season.

Bar the 5-1 home win over Asteras Tripolis which saw Harry Kane score a hat-trick and Erik Lamela net a couple of stunning goals, little has seemed to excite the players. The Besiktas defeat which sent them into second place in Group C might inadvertently have sent them on a route of opponents who will provide the kind of challenges which bring the best out of this side.

Tiredness moving into 2015 could still prove problematic, of course. But should Tottenham embrace the Europa League, a good run could galvanise the side as they continue to realise their identity under Pochettino’s management. At least to the extent they might overlook a few knocks and niggles.

February is a couple of months away, and Tottenham have a lot of football to play before then. We will see what shape they are in by that point, and how that too will inform their approach to the knockout stages of the Europa League.

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