Top 5 Champions League quarterfinal upsets
#4 Dynamo Kiev 3-1 Real Madrid: 1998-99
Real Madrid has faced Dynamo Kiev ten times in European competitions and has remained unbeaten nine times. But the lone defeat eliminated Los Merengues from the 1998-99 Champions League at the quarter-final stage. The reason for Kiev's success - Goals from a 22 years old striker named Andriy Shevchenko.
Shevchenko had been with Kiev since the age of 10 and had a scoring rate of one goal every two games for the senior side. But even with 'Sheva' in the team, Kiev had barely qualified for the main draw of the competition, having been just two minutes away from elimination at the hands of Sparta Prague in the second qualification round.
After yet another sluggish start in the group stages, Dynamo eventually found their rhythm - winning their group and eliminating Arsenal along the way. But the quarter-final draw placed them against defending champions Real Madrid which seemed to signal the end of festivities for Shevchenko and co.
But the first leg at a sparsely occupied Santiago Bernabeu did not go according to plan for Real as Sergei Rebrov put Shevchenko clear to give Kiev the lead. Real would equalise immediately, but the 1-1 draw would leave the tie finely balanced going into the return leg.
The Spaniards were treated to a quite a spectacle in Ukraine as the Olympic stadium in Kiev was packed to the hilt by rowdy Dynamo supporters. All the pressure from a Real squad comprising of Davor Suker, Raul and Morientes could not break down a resolute Dynamo defence. To make matters worse, goalkeeper Bodo Illgner conceded a penalty for pulling down Shevchenko in the area in the 62nd minute.
In front of 80,000 supporters, Shevchenko appeared to fluff his chance when Illgner dived low to the left to keep out the spot kick. But Illgner couldn't hold on to the ball and Shevchenko made no mistake from the rebound to send the home fans into a frenzy.
11 minutes later, Shevchenko scored his third goal of the tie from an exquisite Rebrov pass to put the result beyond doubt. A 3-1 aggregate victory took Kiev to a first European Cup semifinal in 12 years and the significance of the result was never more apparent than when Ukranian president Leonid Kuchma entered the dressing room and kissed coach Valeriy Lobanovskyi on the cheek three times.
Kiev would be narrowly beaten by Bayern Munich in the semifinals, but Shevchenko would win the Golden boot and embark on his legendary run with A.C Milan at the end of the season.Modified 20 Dec 2019, 15:16 IST