Leeds lose 4–0 in Barcelona, then go all the way to the Champions League semi-final

Third place in 1999–2000 took Leeds United into the Champions League, and the club spent heavily. Olivier Dacourt came from Lens and Mark Viduka from Celtic. Dominic Matteo arrived too. In November 2000 Rio Ferdinand joined from West Ham United for £18 million, a British record, and in December Robbie Keane came from Inter, on loan at first. Viduka finished the season as the club's top scorer, with 17 league goals and 22 in all.

Leeds beat 1860 Munich home and away in the qualifying round and were drawn in a group with Barcelona, Milan and Beşiktaş.

Barcelona and Milan

They began at the Camp Nou on 13 September 2000 and lost 4–0. Rivaldo scored after ten minutes, Frank de Boer added a free-kick, and Patrick Kluivert scored twice late on.

Six days later Milan came to Elland Road. With a minute left Lee Bowyer tried a shot from long range, and the Milan goalkeeper Dida let it get away from him and over the line. Leeds won 1–0. A week after that they beat Beşiktaş 6–0.

Barcelona came to Leeds on 24 October. Bowyer scored early with a free-kick, and for more than 90 minutes Paul Robinson kept Barcelona out. In the fourth minute of stoppage time Gerard's header hit the post and Rivaldo scored from the rebound. "Their coach will say there should have been 10 minutes of added time," said O'Leary, "but I couldn't understand the four minutes." Jonathan Woodgate said: "All the lads are gutted."

It meant Leeds needed a point in the San Siro on 8 November. Just before half-time Bowyer took a corner from the right, and Matteo got in front of his marker at the near post and glanced a header inside the upright. Serginho equalised in the second half, but 1–1 was enough. Milan won the group and Leeds finished second, a point ahead of Barcelona, who beat Beşiktaş 5–0 that night and went out.

Rome

The second group stage put Leeds with Real Madrid, Lazio and Anderlecht, and it began with a 2–0 home defeat by Madrid. On 5 December Leeds went to the Stadio Olimpico and played the Italian champions. With ten minutes left Harry Kewell started a move, Viduka backheeled the ball on, and Alan Smith scored. Lazio 0 Leeds 1.

In February Leeds beat Anderlecht 2–1 at Elland Road and 4–1 away. They lost 3–2 in Madrid and drew 3–3 with Lazio at home, and finished second behind Real Madrid, four points clear of Anderlecht.

Deportivo

The quarter-final was against Deportivo La Coruña. At Elland Road on 4 April 2001 Ian Harte scored with a free-kick after 27 minutes, Smith added a second after half-time, and Ferdinand scored his first goal for the club in the 66th minute. "This is possibly the best night in Europe for us this season," said O'Leary. "But it's only half-time."

In La Coruña Deportivo won 2–0. Leeds went through 3–2 on aggregate.

Valencia

The semi-final first leg, at Elland Road on 2 May, finished 0–0. During it Bowyer stamped on Valencia's Juan Sánchez, and the referee, Pierluigi Collina, took no action. UEFA looked at the video, found Bowyer guilty and banned him for three matches. The ban was announced the day before the second leg.

At Mestalla on 8 May Sánchez scored after 16 minutes. Leeds protested that he had handled, and replays showed the ball had come off his shoulder and upper arm. Early in the second half Sánchez scored again, and Gaizka Mendieta made it 3–0. Near the end Smith was sent off for a two-footed tackle on Vicente.

"We got punished by video evidence over Bowyer," said O'Leary, "but there is nothing comparable available for what was a disgraceful decision on the first goal." Of Valencia he said: "They're a fantastic side and I hope they go on and win the final." They lost it to Bayern Munich on penalties in Milan.

One point

In the Premier League Leeds finished fourth with 68 points, one point behind Liverpool and short of a second Champions League campaign.

In the autumn of 2001 they bought Seth Johnson from Derby County and Robbie Fowler from Liverpool, Fowler for £11 million. On New Year's Day 2002 Leeds were top of the Premier League.

Hull Crown Court

Through all of this, two of O'Leary's players had been facing a criminal trial. In January 2000 an Asian student, Sarfraz Najeib, was attacked near a nightclub in Leeds and left with a broken nose, a fractured cheekbone and a broken leg. His brother was also beaten. Bowyer and Woodgate were charged with causing grievous bodily harm with intent and with affray. The club refused to suspend them while the case went on, saying they were presumed innocent.

The first trial, at Hull Crown Court, collapsed in the spring of 2001, after the Sunday Mirror published an article in which the student's father said the attack had been racially motivated. The judge ordered a retrial.

The verdicts came on 14 December 2001. Bowyer was cleared of both charges. Woodgate was cleared of grievous bodily harm with intent but convicted of affray, and he was ordered to do 100 hours' community service. Paul Clifford, a friend of Woodgate's, was jailed for six years. Afterwards Leeds fined Bowyer four weeks' wages for breaching the club's code of conduct. He refused to pay and was put on the transfer list, and came off it when the dispute was settled.

The book

In January 2002 O'Leary published a book, "Leeds United on Trial". In it he called the attack "senseless violence" and criticised Bowyer and Woodgate for "failing to exercise control" that night. He criticised them in a Sunday newspaper article too. Many commentators suggested it was a step too far in the eyes of the chairman and the board, and relations between O'Leary and his dressing room were said to have broken down.

Leeds did not stay top. They finished the season fifth, and out of the Champions League for a second year.