Former European champions Barcelona, Juventus and PSV Eindhoven all crashed by the wayside on Wednesday as the 16-team line-up for the second phase of the Champions League was finalised.
But while Barcelona and Eindhoven had the consolation of being able to continue their European ambitions in the UEFA Cup, Juventus were totally eclipsed after finishing bottom of their group and having two players sent off for the second successive European match in a 3-1 defeat at Panathinaikos.
With 12 berths already decided, there were four places still to be filled on Wednesday and Leeds United, Manchester United, Anderlecht and Panathinaikos duly took them.
LEEDS END ALL TALK OF INCENTIVES
Leeds United reached the second phase for the first time on Wednesday when their 1-1 draw at AC Milan was enough to secure them second place in Group H and end the hopes of Spanish giants Barcelona, European champions in 1992.
The result also ended all speculation that AC Milan would play all out to crush the English side despite already having won the group, after reports they had been offered huge cash incentives by Barcelona to do so.
Barcelona would have qualified for the last 16 if Milan had beaten Leeds and Barcelona beaten Besiktas but although Barcelona did beat Besiktas 5-0, Milan missed a penalty and trailed to a 45th-minute Dominic Matteo goal at the San Siro until Serginho equalised for the Italian side after 68 minutes.
That was the end of the scoring and at the end of the match Milan and Leeds were through and Barcelona were eliminated from the first stage of the Champions League for the third time in four attempts.
THREE ENGLISH TEAMS THROUGH
Leeds joined English rivals Manchester United and Arsenal in the second phase after United beat Dynamo Kiev 1-0 to secure second spot in Group G. Arsenal's place as group winners was already secured.
United had to win at Old Trafford to qualify for the last 16 and an 18th-minute goal from Teddy Sheringham proved the difference between the sides.
Kiev's best chance came five minutes from time when substitute George Demetradze sidefooted wide from close range with only goalkeeper Fabien Barthez to beat.
The three points gave United 10 points and the runners-up spot behind Anderlecht who beat PSV Eindhoven 3-2 in a thrilling match in the Netherlands.
Anderlecht built a 2-0 lead through Bertrand Crasson and Jan Koller after 37 minutes but PSV fought back to equalise with two goals from Adil Ramzi.
With the end of the match just seconds away and a draw looking the most likely result, PSV had Kevin Hofland sent off for a second yellow card and Anderlecht substitute Souleymane Youla scored the winner.
PSV go into the UEFA Cup, while Kiev are eliminated.
HAMBURG SETTLE FOR THIRD
The other main drama of the night centered on Group E.
Deportivo Coruna had already clinched first place but Juventus, Panathinaikos and Hamburg SV were all in contention for the runners-up spot.
For much of the night it appeared Hamburg were going to grab it as they led Deportivo from the 10th minute when Mehdi Mahdavikia put them ahead.
And while Panathinaikos and Juventus were drawing in Athens, Hamburg were effectively second. But then everything changed within 10 minutes halfway through the evening.
Panathinaikos scored twice in eight minutes to race into a 3-1 lead over Juve, while Deportivo equalised against Hamburg at almost the same time.
With the matches ending 1-1 in Hamburg and 3-1 to Panathinaikos in Athens, the Greeks joined Deportivo in the last 16, Hamburg were in the UEFA Cup and Juventus eliminated.
WOEFUL FOR JUVE
The evening was truly woeful for the Italians.
For the second successive Champions League match they ended with nine men after goalkeeper Edwin Van der Sar and striker Darko Kovacevic were sent off.
Two weeks ago Zinedine Zidane and Edgar Davids were both sent off when Juventus lost 3-1 at home to Hamburg.
The other two matches merely confirmed the final pecking order in Group F with with Helsingborg drawing 1-1 with Paris St Germain and Rosenborg Trondheim drawing 1-1 with Bayern Munich.
Bayern took first place by a point from PSG with Rosenborg going into the UEFA Cup and Helsingborg into a long dark Swedish winter.
The draw for the second phase of the Champions League and the third round of the UEFA Cup takes place in Geneva on Friday.