Perhaps this what they mean when they speak of the importance of qualifying for the Champions League. Milan away, in the last sixteen of what is, for better or for worse, Europe’s premier club competition. The San Siro excels in evenings of high drama – it could even be argued that it is architecturally theatrical – and there are few clubs on the whole continent as experienced in this particularly rarefied air as Milan. Yet tonight, Tottenham Hotpur, for five full decades the bridesmaids of London football, never mind English or European football, gate-crashed the party and came away with a win that ranks alongside the cream of anything that they have managed during their years in the relative wilderness.

Moreover, this was a Spurs team shorn of its creative heartbeat. Luka Modric, the waif-like genius through whom so much of their best football is played, and Gareth Bale, whose masterclass against Internazionale brought him to the attention of a full continental audience for arguably the first time, were both missing from this evening’s team. In other words, this was a Spurs starting eleven that could only scrape out of what could be described as third gear. Tonight, however, they made the best of these shortcomings, and played taut, attractive football of a type that few have managed to pull off against Milan at this venue over the years.

Milan, however, were pedestrian tonight, especially for a team that is currently three points clear at the top of Serie A. Whilst Spurs were playing football that was smart and economical, Milan plodded around the San Siro pitch as if wearing lead-filled boots. For all of this, however, arguably the best two chances of the match fell to the home side, both headers that the Spurs goalkeeper Heurelho Gomes did outstandingly well to keep out but, other than that, Milan looked as limp as lettuce. Spurs, meanwhile, managed a couple of chances of their own, most notably for Rafael Van der Vaart, and Aaron Lennon also impressed on the right-hand side for the visitors.

The defining moment of the match – at least from a pure football perspective – came with ten minutes left to play. Lennon broke on the right-hand side and fed the ball into the middle. Peter Crouch, who had hitherto this evening shown much of the mobility of a scarecrow made of coat-hangers, must have been delighted to find that his marker had momentarily traded his Milan kit for a nineteenth century diving suit, and took advantage of the relatively simple task of rolling the ball into the empty goal. There was still time for the Milan to force a chance to draw level, but Zlatan Ibrahimovic’s push upon Michael Dawson was well spotted by the referee and the crescendo of noise that accompanied the ball hitting the back of the net quickly fell away to silence.

For all of their imperiousness – let us not forget that not only is this team top of Serie A, but this is a club that has won seven previous European Cups – there was something unlikable about Milan this evening, a petulance that discredited the club. Matthieu Flamini’s two-footed lunge at Vedran Corluka could – probably should – have resulted in a red card, but this was a mere sideshow in comparison with Gennaro Gattuso’s second half feud with one of Harry Redknapp’s assistants, Joe Jordan. Just before the hour, Gattuso shoved Jordan in the face and tempers flared again at the end of the match, resulting in Gattuso appearing to head-butt Jordan.

As much as we might even grudgingly admire the brass neck of anybody brave enough to take a pot shot at – the frankly, let’s face it, slightly scary-looking – Jordan, it is impossible to condone such behaviour and it is not difficult to imagine that UEFA may hold a similar opinion on the matter. Such petulance deserves any sanction that follows over the next few days, but the fact of the matter is that the most damning indictment of this Milan team comes with the final score itself. Out-thought and outplayed by a Spurs team missing its two most creative players, they will now have travel to White Hart Lane and win the second leg, probably without conceding a goal. The Spurs defence has had its moments of leakiness this season, but this still feels like an uphill battle for them.

Spurs supporters will already be fully aware of the fact that they could yet toss this glorious lead away in the second leg. Tonight, however, they will not be overly concerned over such matters. They have now beaten both of the Milan giants in this year’s Champions League – the reigning champions of Europe and the current leaders of Serie A – and the boost to their confidence could be such that they may even start to think that their team could get to the business end of the competition in their first attempt at it that anyone below the age of sixty can remember. A step too far? Maybe, but, as anybody that follows Tottenham Hotspur will be more than happy to explain, to dare is to do.

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