In the 1960s, British Prime Minister Harold Wilson apparently made the claim that a week is a long time in politics. If that is the case, how does one begin to sum up the first five months of 2006 for Middlesbrough Football Club?

The winter of the 2005/06 season was very much one of discontent for the Teessiders, who went two months and nine matches without a Premier League win either side of New Year’s Day. That slump included a 7-0 shellacking by Arsenal, which came a week after Steve McClaren’s men had been held to a draw by non-league Nuneaton Borough in the FA Cup, thus necessitating a replay. The pride in reaching the knockout stages of the UEFA Cup without even conceding a goal had very much been dented.

A comfortable win over rock bottom Sunderland, statistically one of the worst teams in Premier League history, brought only temporary solace. The afternoon of 4 February 2006 was a dark one in many ways for ‘Boro. A litany of defensive disaster classes were seized upon by a rampant Luke Moore, who helped himself to a hat-trick in a 4-0 romp for Aston Villa that left the Teessiders teetering just above the drop zone. McClaren did not spare his team in his post-match assessment.

Two moments from that gloomy Saturday summed up the severity of Middlesbrough’s plight. As a cacophony of boos rang around the stadium (or at least those who hadn’t already made tracks for home), one spectator jumped a barrier and hurled his season ticket at McClaren. On the pitch, 17-year-old academy prospect Lee Cattermole was reduced to tears by the toxicity around him.

One must have wondered at that moment how ‘Boro fans were feeling about their following league fixture, a home clash against champions and runaway leaders Chelsea. That turned out to be a pivotal Saturday in the Teessiders’ season.

There were only 78 seconds on the clock when the first goal went in at the Riverside Stadium on 11 February – and it was the home fans who cheered as Fabio Rochemback found a way past the Blues’ defence. The pessimists among the home crowd may have feared it would merely spark Chelsea into life, but instead, it did that to McClaren’s men, who produced one of the shock results of the season in romping to a 3-0 win. To put it in a modern context, it was a bolt from the blue similar to Watford’s result against Liverpool a few months ago,

given the teams’ respective form and league positions.

That result started a run of five wins in seven league games, which would ultimately divert them comfortably away from the drop zone in the Premier League. However, the final three months of their season would be defined by what happened in European competition. Their round of 32 UEFA Cup tie pitted them against a Stuttgart side who had made the knockout stages of the Champions League just two years previously, and would go on to win the following season’s Bundesliga – no easy meat, then.

Buoyed by their shock win over Chelsea, Middlesbrough went to Germany and produced an excellent 2-1 win, surviving a late scare after Daniel Ljuboja curled in a free-kick for the hosts. The return leg at the Riverside was a hard watch for the home fans, with McClaren setting up cautiously. Christian Tiffert levelled the tie on aggregate after just 13 minutes, and ultimately ‘Boro were indebted to goalkeeper Mark Schwarzer to see them through on away goals. “Job done”, surmised McClaren afterwards in deadpan fashion.

Roma were next up in the round of 16 and Middlesbrough’s good form rolled on, with an early Yakuku penalty enough for a 1-0 home win. When Jimmy Floyd Hasselbaink headed them in front at the Stadio Olimpico, ‘Boro seemed set for the quarter-finals. However, a brace from Mancini either side of half-time levelled the tie and Schwarzer again came to the fore, making two astounding saves as McClaren’s side again squeezed through, courtesy of the away goals rule.

Middlesbrough had done enough from first-leg wins in those two ties but would have to do it the hard way against Basel in the last eight, losing 2-0 in Switzerland. The task became near-impossible when Eduardo put the visitors ahead at the Riverside in the second leg, with ‘Boro now needing four goals to advance. Two Mark Viduka goals either side of the interval helped, as did the half-time introduction of Hasselbaink as McClaren went three up top, deserting his customary caution.

The dismissal of Danijel Majstorovic and a goal for Hasselbaink to level the tie on aggregate had belief surging through the Teesside venue but, as the clock struck 90, ‘Boro still needed one more goal. Rochemback’s shot was blocked by Pascal Zuberbuhler, but he could only parry it straight to the long-serving Massimo Maccarone, who dispatched the rebound to spark bedlam around the Riverside. Improbably, ‘Boro had made it to the last four of the UEFA Cup, matching the feat of fellow north-east club Newcastle two years previously.

There were some familiar narratives in the semi-final first leg away to one-time European champions Steaua Bucharest, amid an intimidating atmosphere in the Romanian capital. Defeat and the lack of an away goal hurt Middlesbrough’s chances but the margin would have been far wider than 1-0 had it not been for another masterclass from Schwarzer. The second leg would also prompt some senses of déja vu. 

‘Boro fans would have hoped for an early goal and there were two inside the first 25 minutes – but both for Steaua. McClaren’s men again found themselves needing four goals in little more than an hour to keep their European dream alive. Having been thwarted in the FA Cup semi-finals four days earlier, another cup run looked set to come up narrowly short. However, Maccarone soon pulled one back and, buoyed by what happened against Basel, the home side poured forward towards the end of the first half.

After the interval, it was one-way traffic towards Steaua’s goal. The game entered its final half-hour and ‘Boro still needed to score three. Viduka’s 62nd-minute header levelled it on the night. A fortuitous Chris Riggott goal on 70 minutes levelled the tie, and the tide was definitely in Middlesbrough’s favour. However, the clock ticked down with no sign of the decisive fourth goal. Was the Basel comeback too improbable to be repeated so soon?

In the 89th minute, Stewart Downing delivered a cross towards the back post, where Maccarone was waiting. The Italian striker got his head to it and steered the ball past Alberto Carlos and into the Steaua net. The Riverside Stadium erupted, although there were still four minutes of stoppage time to be played. Nicolae Dica nearly broke the home fans’ hearts, but his shot was blocked by Ugo Ehiogu. At the final whistle, which confirmed a 4-2 victory, several ‘Boro players engulfed one another in a celebratory pyramid and ITV commentator Jon Champion summed up the moment as “brilliant, unbelievable, historic, hysterical, magnificent”. He wasn’t exaggerating.

Having passed that variety of tests so dramatically, Middlesbrough need not have held out much fear as they travelled to Eindhoven to face Sevilla in the final, which would be McClaren’s last game in charge before embarking on an ill-fated spell as England manager. The Spanish side was a cut above any team ‘Boro had faced thus far, though, and were good value for the lead they took in the 26th minute through Luis Fabiano. McClaren later brought two strikers on from the bench in pursuit of an equaliser and, at 1-0 going into the final 15 minutes, the contest was still alive.

Sadly, Middlesbrough ran out of steam and Sevilla took full advantage, scoring three more times as the Teessiders were subjected to a heavy defeat that they did not deserve. It was an anticlimactic end to a truly extraordinary European adventure and, unlike a previous 4-0 defeat only three months previously, this one didn’t come with McClaren being the target of an airborne season ticket thrown in rage. 

As if the journey to Eindhoven wasn’t remarkable enough for the Middlesbrough fans who experienced it, the UEFA Cup run would seem all the more special in subsequent context as the club lost their Premier League status three years later, and have only been back for one season since – there has even been a battle to avoid relegation from the second tier this term. How unlikely those nights against Basel and Steaua would have seemed on that February afternoon when Cattermole cried and season tickets were aimed at McClaren. 

How long ago it must feel for their manager, who after his fine spell on Teesside, had an England spell best remembered for his ill-advised use of an umbrella, on the night that defeat to Croatia at Wembley ended hopes of Euro 2008 qualification, prior to forgettable stints at Wolfsburg, Nottingham Forest, Derby (twice), Newcastle and QPR. 

Middlesbrough’s odyssey to Eindhoven was brilliant, unbelievable, historic, hysterical and magnificent indeed.