'The greatest comeback since Lazarus!' Boro's 2005/06 European Fairytale

When Middlesbrough left the Stadio Olimpico in March 2006 with an away goal-aided triumph over Roma in the Last 16 of the UEFA Cup, you would have been forgiven for thinking that was the best it could get for the Teessiders in Europe. Against a historically renowned Roma side: that had reached a European Cup final; had won a Serie A title in the past five years; and had a squad comprising Francesco Totti, Samuel Kuffour, and Vincenzo Montella, Boro would progress despite a 2-1 defeat in the Italian capital.

Even manager Steve McClaren felt that this was the pinnacle of a remarkable season. ‘You don't have nights like this very often in your career; it ranks as one of the best in mine’, said the future England head coach. Yet, this was going to be European campaign so monumental that this triumph over Roma wasn’t even going to be the talk of Teesside a few weeks later. A European season so memorable that it’s easy to forget that in this same campaign, Boro scored league victories over Manchester United, Chelsea, and Arsenal, two of which were three-goal hammerings.



The 2005/06 UEFA Cup campaign was a second in a row for Boro, who had won their first major trophy by beating Bolton in the League Cup final in 2004. The European campaign that followed saw them reach the Last 16, only to lose out to Sporting Lisbon. But they’d be back in Europe’s secondary club competition the following year, this time by virtue of finishing seventh in the Premier League in 2005.

Boro’s 2005/06 European campaign began with a qualifying tie against Greek side Skoda Xanthi in September. Goals from George Boateng and Mark Viduka was enough for a 2-0 win at the Riverside in the first leg, and a goalless draw in the return fixture gave them passage to the group stage.

If Boro fans thought the UEFA Cup was meant to be a side attraction, with fun away trips but an inevitably early end, they were happily mistaken. This was Boro at arguably their peak, but they still weren’t expected to go quite far, and losing to Sporting in 2005 seemed like the farthest they could get on the continent. However, by the end of matchday two, McClaren’s side were two for two in terms of wins, first narrowly seeing off Grasshoppers in Turin, then putting three past Ukrainian side Dnipro, the latter victory coming thanks to a Viduka brace. Then came a barren draw against AZ – a game tarnished by the fatal stabbing of a Boro fan before it kicked off – which guaranteed them a place in the knockout phase.

A final group game win against Litex was academic, but it marked something; the beginning for Massimo Maccarone in this European campaign. Before the 2005/06 campaign, the Italian was something of an also-ran. Maccarone began his career with Milan, but made zero appearances, and after a few loan spells, ended up at Empoli. Two years at Empoli saw the ‘Big Mac’ – as he’d become known – bag 36 league goals, resulting in an £8million-pound move to Teesside.

But Maccarone didn’t quite live to expectations at Boro, and for a club that had been thrilled by Fabrizio Ravanelli in the late 90’s, this particular Italian wasn’t the poster boy for glamour. So, came a couple of loan moves for the 2004/05 season, first to Parma, then to Siena. The skinhead forward would return the following season, but in a squad that had Viduka, Yakubu and Jimmy Floyd Hasselbaink in attack, he was always going to find first-team opportunities hard to come by. Yet, the fact that he became a fan favourite despite not starting often made it all the more romantic, and in the Litex game, two goals in the final ten minutes at the Riverside – one of which was a peach from over 20 yards – was a kind of trailer of what was to come in the latter stages of the competition.

It took Massimo a while to get going on Teeside

Before Maccarone could begin his heroics, Boro dropped a statement when they went to Stuttgart in the first leg of the Round of 32, and won, via goals from Hasselbaink and Stuart Parnaby. The second leg was rather nervy, as they conceded early on to Christian Tiffert, but held on to find themselves in the last 16 thanks to the away goals rule.

The second knockout round was surely going to be a bridge too far. Next up were Italian giants Roma, who had as many European finals as Boro had European appearances. Even when Boro edged out the Giallorossi in the first leg, thanks to a Yakubu penalty, they were still outsiders, as many noted, like the Daily Mirror, whose headline for the game was ‘WHAT A SCALP’. For Roma manager Luciano Spalletti, there was still confidence in the Italians progressing. ‘Boro are also strong, physical and difficult to play against, but I'm still confident’, said Spalletti. ‘It will be a real humdinger of a game over there’, said Boro skipper Gareth Southgate.

Boro had fans believing when Hasselbaink headed them in front after half an hour in Rome. Was this really on? Roma would hit back, Mancini equalising on the night just before halftime, then scoring a penalty in the second period. McClaren would watch his side hold on for a famous night. ‘The flares and fireworks unleashed by Roma's ultras last night were intended to intimidate Middlesbrough’, wrote The Guardian’s Louise Taylor on the night. ‘Instead they simply illuminated Steve McClaren's side's achievement in reaching the quarter-finals as Luciano Spalletti's Italians were hoist by their own counter-attacking petard’.

Boro had done it. Against all the odds, in their second ever European season, they were heading for the last eight. Basel looked like a relatively easier task than Roma on paper, but two goals late in the first half of the first leg, from Matias Delgado and David Degen, had Boro on the brink of elimination. For the first time in the UEFA Cup that season, Middlesbrough had to respond to a setback, as they prepared for a second leg at home with a 2-0 deficit to overturn.

If the task was difficult, it was nigh-on impossible when Eduardo put Basel in front midway through the first half of the second leg. Now Boro were three down on aggregate, and thanks to the away goals rule, needed to score four goals in 67 minutes. This was a true mountain to climb. But Boro began their journey upwards when Mark Viduka levelled on the night 12 minutes before halftime. 12 minutes after the break, Viduka was on the score-sheet again, and 12 minutes either side of the interval saw Boro halve their deficit. Hope became belief when Hasselbaink rifled a belter from 20 yards with eleven minutes to play.

Boro were within one of the impossible, but time was running out, and they looked to have run out of legs. Enter Maccarone. In the final minute, Fabio Rochemback was teed up by Hasselbaink, and his shot was pushed out by Basel goalkeeper Pascal Zuberbuhler. The rebound dropped to Maccarone, and his shot found its way into the bottom corner via the fingertips of Zuberbuhler. ‘Hats off! Hats off!!’ yelled Peter Drury in the commentary box. Off went Maccarone’s shirt, and the Boro fans went berserk. They were heading for the last four of a European competition.

No matter what happened next, this was a monumental season. Boro had beaten Stuttgart, Roma, and now performed a miracle against Basel. Up next was Steaua Bucharest, European Cup winners in 1986. A team who won the European Cup at a time when their English opponents stared liquidation in the face. Boro had created the thrill of the season, and would have had a tinge of optimism despite a 1-0 loss in the semi-final first leg as they welcomed the Romanians to the Riverside in late April.

Going into the second leg, Boro had first-choice goalkeeper Mark Schwarzer unavailable, as well as key defender Emmanuel Pogatetz. Those losses seemed even more pivotal when, thanks to some sloppy goalkeeping from reserve goalie Brad Jones and some slack defending, Steaua were two up on the night inside 24 minutes, with goals from Nicolae Dica and Dorin Goian.

Boro were two down, and like the Basel second leg, needed to score four goals in 67 minutes without reply. But unlike the Basel game, they’d looked hapless for the first 25 minutes. Perhaps they had run out of miracles. Maybe there was no longer a Hail Mary to throw. So, about a bold call instead? Not long after Steaua’s second goal, McClaren took off Southgate – who had damaged a hamstring – at centre-back and brought on Maccarone, and the substitute justified that change moments after by halving the deficit on the night.



Boro still had a long way to go, but they’d done this before, and when Viduka headed in Stewart Downing cross in the 65th minute, it looked very much on. Then, Boro, with Yakubu on the pitch, played their final attacking card, and Steaua didn’t seem to be able to get out of their own defensive third. Chris Riggott made it 3-2 Boro on the night, with 16 minutes left, and then came stoppage time. Another Downing cross, this time it went to the back post, and was met by the head of Maccarone. For the second time in April of ‘06, Maccarone had sent the whole of the Riverside berserk. ‘Massimo, I love him till I die’, said Hasselbaink afterwards. For the second time in a month, Middlesbrough had faced a mountain, dared to believe, and climbed it. ‘It is a brave man who says Boro will not win in Eindhoven’, said Michael Walker of The Guardian after the semi-final.

So, off to Eindhoven for the final, against Spanish side Sevilla. But such is the cruelty of football that, right at the last, it can laugh in the face of a building narrative, scorn with derision at a potential fairy-tale. As much the beautiful game gives, it does its fair share of ripping away, and Boro went into the break a goal behind, via a brilliant Luis Fabiano header. And when Enzo Maresca added a second for the Spaniards, there was going to be no comeback this time. Boro had truly used their nine lives.

There was still time for Sevilla to add two more goals, and cruise to their first of six UEFA Cup victories. In spite of a grim night for Boro, it takes nothing away from a spectacular journey. Perhaps it even buttresses it, sometimes glorious failure is as fond a memory as euphoric triumph. For Boro, this was about the memories; about making the noise in Rome, and shaking the Riverside to its core. It was about ‘Big Mac’ and ‘Big Mark’, and the most beautiful of miracles.

Boro haven’t been to the continent since, and have actually suffered two relegations since the 2005/06 season. But that does next to nothing to taint a beautiful picture that was painted. From Xanthi to Eindhoven, via Stuttgart, Rome and Bucharest, for nine months, Middlesbrough felt alive.


This piece was kindly written for @TFHBs by Kunle Ajao - you can follow him on twitter @_KunleAjao

©The Football History Boys, 2020

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