The Merseysiders were defending champions that year after their heroics against Milan in Istanbul, but were unceremoniously dumped out by the Portuguese side.
A toothless display was punished by two stunning goals from Simao and Fabrizio Miccoli.
2) FC Basel 2-1 Manchester United, December 7, 2011
This result will still be fresh in Sir Alex Ferguson’s mind as his side are forced to face Ajax in the Europa League.
The Red devils were wasteful with possession and chances for most of the game, so it was not a great surprise when Alexander Frei and Marco Streller capitalised on losses of concentration from United’s defence and goalkeeper to send them out of the competition at the first hurdle.
3) Chelsea 1-1 Rosenborg, September 18, 2007
This was Jose Mourinho’s last game in charge of the Blues and it was a dismal affair. The Norwegians took the lead midway through the second half and, although Chelsea did equalise through big money flop (familiar?) Andriy Shevchenko, the response was feeble.
The already bad atmosphere was compounded by the fact that Stamford Bridge was half-empty.
4) Real Madrid 4-0 Tottenham Hotspur, April 5, 2011
It may seem harsh to condemn Spurs in their first time playing at the illustrious Bernabeu, but this was after they had won 1-0 in Milan in the round before.
Peter Crouch set the tone for a calamitous display when he managed to pick up two silly bookings in the first 15 minutes, as Emmanuel Adebayor’s brace helped the Spanish side trample over Harry Redknapp’s side.
5) Spartak Moscow 4-1 Arsenal, November 28, 2000
Arsenal have never fared too well when playing behind the old iron curtain, but this was a display of exceptional haplessness.
The Gunners even took the lead through Brazilian left-back Sylvinho, but the sub-zero temperatures took their toll and the north Londoners whimpered to a thrashing at the hands of the Russians.
In additional, Arsenal once again humiliate by the Italian giants, AC Milan at the Round of 16 2011-12 Champions League. They lost with a big amount of goals, 4-0. Boateng & Ibrahimovic scored a piece while Robinho struck twice.
SOURCE: GiveMeFootball.com
