Dynamo Kyiv 3-3 Bayern Munich – semi-final first leg, 7 April 1999

Dynamo Kyiv’s wonderful team of the late 1990s deserved a Champions League final – but on a pulsating night at a packed Olympiyskiy they threw away the best chance they would ever have. It was exquisite fare for much of the evening and, when Andriy Shevchenko squeezed in his second goal of the night two minutes before half-time, seemed to be going precisely as the old master Valeriy Lobanovskiy had designed. Moments later Michael Tarnat’s daisycutter of a free-kick restored some doubt but Vitaliy Kosovskiy’s 50th-minute goal – capitalising on some sloppy defending – suggested Dynamo would cut loose. But this was an excellent Bayern side and they fought back with two goals in a frantic last 12 minutes. First Stefan Effenberg curled Bayern’s second successful set-piece of the night inside the near post; then Carsten Jancker poked out a leg for 3-3. You feared it might be decisive, and Bayern went on to make sure by winning the second leg 1-0.

Juventus 2-3 Manchester United (Manchester United win 4-3 on aggregate) – semi-final second leg, 21 April 1999

It was quite the year for compelling semi-finals. While the most dramatic night of all was still a month away, this was the match that led United to believe anything might just be possible. Missing the injured Ryan Giggs, who had equalised what seemed a crucial Antonio Conte goal at Old Trafford, they quickly went two goals down at the Stadio delle Alpi to two Filippo Inzaghi goals – the first saw the striker doing what he did best from a matter of millimetres, the second cruelly deflected off Jaap Stam. This was a formidable Juventus side and the game appeared to be up, but Roy Keane’s 24th-minute header quickly changed the complexion. Ten minutes later Dwight Yorke gave United an improbable away-goals lead from Andy Cole’s cross and, having held out commendably in the second half, they made it safe late on when Cole slotted into an empty net. This, of course, can only partly tell the tale of a defining and unbearably tense affair.

Manchester United captain Roy Keane wheels away after giving his side hope in their 1999 semi-final second leg in Turin. They would complete a comeback from 2-0 down to win 3-2 against Juventus.
Manchester United captain Roy Keane wheels away after giving his side hope in their 1999 semi-final second leg in Turin. They would complete a comeback from 2-0 down to win 3-2 against Juventus. Photograph: Getty Images

Milan 3-3 Liverpool (Liverpool win 3-2 on penalties) – final, 25 May 2005

The standard by which major finals have been judged since, which is pretty unlucky for most. It has all been said before, but so many people have an anecdote about switching over at half-time or occupying themselves elsewhere after the most one-sided of first halves and the fact that, by the time Vladimir Smicer scored Liverpool’s second in the 56th minute, they were all scrambling back to their sofas speaks of the sheer implausibility of what happened. By then Xabi Alonso’s equaliser – after his penalty had been saved, because nothing was to be straightforward in Istanbul – seemed inevitable. The Steven Gerrard-inspired comeback had brought plenty of heroics but everyone has their own favourite moment and the individual acts of inspiration that followed – Djimi Traoré’s goalline clearance, Jerzy Dudek’s saves from Shevchenko in open play and the shootout – added to the legend.

Istanbul and all that: Liverpool celebrate with the trophy after their remarkable win over Milan having trailed 3-0 at half-time in the 2005 final.
Istanbul and all that: Liverpool celebrate with the trophy after their remarkable win over Milan having trailed 3-0 at half-time in the 2005 final. Photograph: Tom Jenkins for the Guardian

Chelsea 4-4 Liverpool (Chelsea win 7-5 on aggregate) – quarter-final second leg, 14 April 2009

The frequent Champions League match-ups between these two had begun to test the patience but this more than made up for the generally attritional fare of previous years. Chelsea had won 3-1 at Anfield and seemed good for the last four, but with John Terry and Steven Gerrard both missing it was as if the teams had been allowed to run around unsupervised in the second leg. Liverpool were two up within half an hour through Fabio Aurelio and a Xabi Alonso spot-kick; Chelsea, roaring back in a game that at times resembled a pinball match, replied through Didier Drogba, Alex and Frank Lampard – and with 14 minutes to play that appeared to be that. But a deflected shot from Lucas and a Dirk Kuyt header suddenly pulled Liverpool to within a goal of the last four once more – but as they pushed for the winner Lampard swept in Chelsea’s fourth and stopped short a comeback to rival that of Istanbul.

Liverpool’s Pepe Reina looks back in despair as he concedes another goal against Chelsea in 2009.
Liverpool’s Pepe Reina looks back in despair as he concedes another goal against Chelsea in 2009. Photograph: Jamie McDonald/Getty Images

Arsenal 2-2 Barcelona – quarter-final first leg, 31 March 2010

Arsenal came out dazed, blinking and – for a week at least – alive. For three-quarters of this game Barcelona put on a show to rival anything they produced at their peak, cutting the home side to pieces during a first half that somehow ended goalless before Zlatan Ibrahimovic found his range with two goals shortly after the interval. The tie seemed dead already; Barcelona should, in truth, have been several more to the good and only a virtuoso performance by Manuel Almunia had kept things vaguely competitive. Then, out of nowhere, Theo Walcott planted a low drive under Víctor Valdés. Arsenal’s tails were up for the first time in the game, and with five minutes to play Cesc Fàbregas was fouled in the box by Carles Puyol, who was sent off. Fàbregas drilled in the penalty; no one knew at the time that he had fractured his fibula under Puyol’s challenge. It was a heroic end to a dizzying night, but Barcelona cut loose to win the second leg 4-1.

Cesc Fàbregas of Arsenal is brought down by Carles Puyol of Barcelona. Fàbregas scored the resulting penalty to earn a 2-2 draw for Arsenal, even though the tackle had fractured his fibula.
Cesc Fàbregas of Arsenal is brought down by Carles Puyol of Barcelona. Fàbregas scored the resulting penalty to earn a 2-2 draw for Arsenal, even though the tackle had fractured his fibula. Photograph: Shaun Botterill/Getty Images

Borussia Dortmund 3-2 Málaga (Dortmund win 3-2 on aggregate) – quarter-final second leg, 9 April 2013

Had Felipe Santana not scored three minutes into injury-time – almost certainly from an offside position – and sent Signal Iduna Park into paroxysms of joy then Borussia Dortmund’s story under Jürgen Klopp would be missing perhaps its most romantic chapter. They went on to overwhelm Real Madrid and face Bayern Munich at Wembley but for most of this second leg, which followed a goalless game in Spain, nothing came easily. A relatively drab first 25 minutes had been lit up by a goal from Málaga’s Joaquín, cancelled out by Robert Lewandowski. When Eliseu scored a second for Malaga eight minutes from time, Klopp’s side needed two. It sparked a furious rally, Dortmund throwing everything forward when many sides might have wilted; as the clock passed 90 minutes Marco Reus nudged the door ajar before Santana scored to leave Klopp feeling “the best I’ve ever felt”.

Felipe Santana of Borussia Dortmund scores their winning goal in injury time to complete a remarkable comeback against Málaga and reach the 2013 semi-finals.
Felipe Santana of Borussia Dortmund scores their winning goal in injury time to complete a remarkable comeback against Málaga and reach the 2013 semi-finals. Photograph: Lars Baron/Bongarts/Getty Images

Bayern Munich 4-2 Juventus (Bayern win 6-4 on aggregate) – last 16 second leg, 16 March 2016

This was a classic between two teams that, for different periods on the night, were on top of their games. Juventus had been outplayed for much of the first leg but battled back to draw from two goals down; a side missing several key players were given little chance at the Allianz Arena but came out flying. When Paul Pogba scored six minutes in, Bayern were in trouble; when Juan Cuadrado finished wonderfully before the half-hour, Juve seemed to have completed the perfect turnaround. One more goal would have sealed things and, irresistible at this point, they spurned chances to score it. Instead it would be Bayern, invisible as an attacking force for an hour, who flipped things around again. Robert Lewandowski pulled a goal back 18 minutes from time and then, with the Italians almost home and hosed, Thomas Müller headed the most unlikely of levellers at the last. Juve were not quite done and had opportunities early in extra time – but Thiago Alcântara and Kingsley Coman, against his parent club, would harness Bayern’s momentum to score in the second period and leave everyone in need of a lie down.

Thiago Alcântara, right, puts Bayern Munich ahead on aggregate in extra time on a memorable night at the Allianz Arena against Juventus.
Thiago Alcântara, right, puts Bayern Munich ahead on aggregate in extra time on a memorable night at the Allianz Arena against Juventus. Photograph: Alexander Hassenstein/Bongarts/Getty Images

Manchester City 5-3 Monaco – last 16 first leg, 21 February 2017

Rarely can two sides with such a mutual disregard for the basic tenets of defending have faced each other in the knockout stage. That made for a breathless, see-sawing night at the Etihad and while the match was peppered with errors both sides needed commending for their commitment to outgunning the other. Monaco, slick and lightning-quick in attack, won plenty of friends but City’s extra experience and quality told in a thrilling comeback from 3-2 down. It would be a quite staggering achievement for the second leg to finish goalless – a fact Pep Guardiola seemed to recognise when saying his team will still need to score in order to progress.