Leeds United's 00/01 European Adventure Part 1: Promise, Tragedy, and the 3rd Qualifying Round.

The 2025-2026 season marks 25 years since Leeds embarked on an unlikely Champions League run which culminated in the club reaching the semi-finals of the competition. What a time it was to be a Leeds fan; exciting young players, throwing money around, mixing it at the right end of the table, and best of all - European football. For myself, the 2000/2001 provided some of my most cherished formative memories as a fan. It wasn't all plain sailing, though; tragedy and off-field issues still haunted the club.

O'Leary Transforms Leeds

After the elevation of David O'Leary from Assistant Manager to Manager, along with a crop of exciting players (often referred to, slightly creepily, as 'O'Leary's babies') looking to break into the first team, Leeds were finally on the up after the demise of the Howard Wilkinson era, and the stifling boredom of the George Graham years. Leeds fans had a team that could get the blood pumping again.

The 99-00 season was not only O'Leary's second season in charge at Leeds, but his second season in charge of any senior team. But the team was flying under his stewardship, as he changed to a more expansive playing style (not exactly difficult after George Graham) and started to introduce promising youngsters like Harry Kewell and Alan Smith.

Leeds finished an impressive 3rd in the league behind Arsenal and Manchester United. This meant a return to the Champions League the following season, having already had a taste of the UEFA Cup. On the face of it, the 99-00 run to the UEFA Cup semi-finals looked like an achievement to be proud of. Results don't tell the full story, though.

Tragedy in Istanbul

In the Semis, Leeds were drawn to play against the second biggest club in Turkey, Galatasaray, with the first leg to be played in Istanbul. What unfolded the night before the first leg in Turkey was beyond anyone's darkest nightmare. As Leeds fans congregated in Taksim Square, they were set upon by some knife-wielding Galatasaray cowards. The attack led to Leeds fans Kevin Speight and Christopher Loftus losing their lives.

Now, I'm not oblivious to the fact that Leeds fans are no angels, who are perfectly capable of finding trouble. But for fans to be attacked and killed, unable to return home to their families, all because of football? That is unfathomable for any civilised person. The two fans who died weren't even involved in the fighting; they were simply in the wrong place, at the wrong time.

Leeds wanted the game to be postponed, and if UEFA had a backbone, or if Galatasaray had a shred of dignity, it would have been. Anyone who follows football to this day, will understand that UEFA is allergic to doing the right thing.

As for Galatasaray, they showed they have about as much class as a shite in a shoe-box. They not only insisted that the game go ahead, but they also refused to have a minute's silence before kick-off or to have their players wear black armbands. Even the simplest mark of respect was beyond them. The whole tragic incident is an irremovable stain on the club and its fan base; a club that truly belongs in the gutters.

After an incident like that, it seems trite to talk about football - it very much becomes an after thought. To no one's surprise Leeds lost the game 2-0; I've watched the highlights back and as the players entered the field, they looked like they'd rather be anywhere else. Who could blame them?

The return leg saw Leeds ban Galatasaray fans from attending the match at Elland Road, which thankfully, after finally finding their collective spine, UEFA supported. The officials from the Turkish club reacted angrily to the ban, because....of course they would. A leopard can't change its spots.

The match ended 2 apiece, with Eirik Bakke scoring both goals for Leeds. It was a painful exit, and an incredibly emotional end to an otherwise successful European campaign, with the young Leeds players being forced to play in conditions that shake even the most hardened of professionals.

A 3rd Place Finish Secures Champions League Qualification

That 2-2 draw did mark an uptick in form for Leeds, however. They'd gone into the game on the back of a 5 game losing streak - which included the game in Istanbul - and they were in danger of missing out on Champions League qualification; something that looked a certainty only a couple of months before. The fact that the team rallied to finish 3rd, especially after what happened in Istanbul, is a testament to the team's spirit and resilience. Having to grow up and mature so publicly can't have been easy for such a young group of players, they deserve massive credit for that.

Big Spenders

With Champions League football secured for the following season, Leeds United's ambitious owners decided to really attack the transfer window, spending money with wanton abandon; of course, at the time everything was rosy in the world of Leeds United, why worry about any possible future consequences?

The first player through the door at Thorp Arch was Olivier Dacourt from French side Lens, for a fee of £7,200,000. Mark Viduka cost £6,500,000, arriving from north of the border after a successful season with Celtic. Leeds then went to Liverpool and spent £4,750,000 on Dom Matteo. Next up, squad player Jacob Burns joined the club from Australian team Parramatta Power for a comparably paltry sum of £250,000. The Jacob Burns signing didn't signal a downturn in spending for Leeds; this wasn't a case of buying key players at the beginning of the window before seeing it out by adding some cheaper squad depth. The biggest was yet to come.

On the 26th of November, Leeds made Rio Ferdinand the most expensive defender in the world, parting with a massive £18,000,000, and £30,000 a week (a £9,000 pay rise) to prise him away from West Ham. Those figures might not sound impressive given the bloated finances of the modern game, but for context: the previous highest fee paid for a defender was the £13,000,000 Roma spent on Walter Samuel, and the previous British record were the £15,000,000 fees spent on Alan Shearer and Jimmy-Floyd Hasselbaink - both strikers.

Lastly, after his initially successful loan, Leeds spent £12,000,000 at the back end of the season to acquire Robbie Keane on a permanent basis from Inter Milan. That took spending to an incredible £48,700,000 over the course of the season. Of course, you wouldn't blink twice at that figure being spent on a single player nowadays, but at the time it was an enormous outlay, demonstrating Leeds' ambition and intent.

The 3rd Qualifying Round

Armed with a young, talented squad, bolstered with expensive new signings, Leeds were ready to take on European football's elite. But before they could mix it in the Champions League proper, they had a 3rd qualifying round to contend with.

The 3rd qualifying rounds were not to be sniffed at back then; it wasn't like the modern Champions League where the biggest clubs are protected and the major leagues take all of the automatic qualifying places. AC Milan, Inter Milan and the previous year's runners-up, Valencia, all had to settle for a 3rd round qualifier, with Inter actually crashing out at the hands of Helsingborgs IF.

1860 Munich

Leeds were drawn against 1860 Munich; not the easiest tie but far from the most difficult. 1860 Munich's history since the 70's may have been littered with relegations and financial issues (something Leeds fans would become accustomed to in the very near future), but the mid-90's saw them turn their fortunes around.

Under the stewardship of President Karl-Heinze Wildmoser and manager Werner Lorant the combination of proven veterans and young talent changed the team from relegation-battlers into a squad that could compete further up the table. This culminated with a 4th place finish at the end of the 1999-2000, and a 3rd round Champions League qualifying tie against Leeds at the start of the following season.

First Leg: Late Goal Gives 1860 Munich A Lifeline

The first leg was drawn to be played at Elland Road, 10 days before the Premier League was due to get under way. 33,769 fans filled a floodlit Elland Road to watch an injury-ravaged Leeds play the team that stood between them and the Champions League group stage. The game looked to be heading towards half-time at 0-0. However, in the 39th minute, Alan Smith capitalised on a woeful back pass to steal in and give Leeds a 1-0 lead. Minutes later, Ned Zelic received a red card for 1860 Munich. A goal and a man up; things couldn't be going much better for the home side at half-time.

The second-half started much the same as the second, with the first real action coming mid-way through. Alan Smith cut inside his man on the edge of the box before stumbling to the ground. The referee pointed to the spot. It looked incredibly harsh on 186-0 Munich; the slow motion showed minimal contact - if any at all - and it was outside the box. The referee was unmoved by the German team's protests and Leeds were delighted to get a chance to double their lead. Ian Harte stepped up and coolly rolled the ball into the opposite corner of the diving 'keeper. 2-0 Leeds.

With less than 20 minutes left, it should have simply been a case of seeing the game out. Unfortunately, nothing is ever simple when it comes to Leeds United. A mere 3 minutes after Ian Harte had given Leeds a 2 goal lead, they were down to 10 men; Olivier Dacourt picked up a 2nd booking for diving. The game was now being played with 10 players apiece. That was until the 83rd minute when Leeds lost another player; this time it was Eirik Bakke's turn to exit the pitch - he picked up a 2nd yellow card after losing out in an aerial challenge.

From being in a position of complete control less than 10 minutes earlier, Leeds now had to play another 6 minutes of regular time, plus the 4 minutes of injury time, with 9 men. An unbelievable act of self-sabotage.

1860 Munich really started to pile on the pressure, but Leeds were holding firm. Then, in the 93rd minute Agostino, 1860 Munich's Australian striker, took advantage of the space afforded to him by getting on the end of a cross first, and heading the ball past Nigel Martyn into the corner. The Germans had their life-line.

Leeds may have won the game, but the mood after full-time wasn't exactly a joyous one after squandering such a comfortable position. Leeds were already struggling with injuries, now they had 2 suspensions to add to their woes as well. David O'Leary was particularly furious, saying in the post match interview: "I'm not very confident about going through............I'm not being defeatist, I'm just being realistic, it's no way to be going into the biggest game this club has had without nine players."

2nd Leg: Smith's Strike Seals Qualification

The following week, Leeds travelled to 1860 Munich's cavernous Olympiastadion with it all to play for. Leeds were missing even more first-team players than the first leg and it showed. 1860 Munich had the better of the opening minutes; veteran midfielder and free-kick specialist Thomas Hassler was a particular threat, hitting the bar and forcing Martyn into some fine saves.

Despite having to soak up early pressure, it was Leeds who extended their lead in the tie. Immediately after the half-time break, Alan Smith pounced on some calamitous 1860 Munich defending, before slotting home. 1-0 on the night, 3-1 to Leeds overall.

There were a few scares to test the nerves of the Leeds fans - Danny Mills and Jonathan Woodgate both had to clear the ball off their own line in the final minutes - but Leeds had done it.

Next stop: the Champions League group stage.....