Five years after beating AC Milan on penalties to lift club football's greatest prize, the Reds face a less glamorous tie against the Super Lig minnows.
Roy Hodgson's side will meet their rivals from Trabzon, who have won the Turkish league six times but not since 1984, at Anfield on August 19 and at the 20,000-capacity Huseyin Avni Aker Stadium a week later.
But the omens and memories must be good for the Reds.
Trabzonspor are managed by Senol Gunes, who masterminded Turkey's third-place finish at the 2002 World Cup.
The teams have met just once before in the second round of the 1976-77 European Cup, with Trabzonspor winning the first leg 1-0 only for Liverpool to prevail 3-0 in the return with Steve Heighway, David Johnson and Kevin Keegan on target.
Liverpool went on to win the first of their five European Cups, with the most recent arriving in Istanbul in 2005.
Aston Villa face a repeat of last season's Europa League play-off after being drawn against Rapid Vienna.
Austria's most successful club with 32 championships progressed to the group stage on away goals at the expense of Martin O'Neill's side.
Villa lost the first leg 1-0 before slumping to a 2-1 defeat in the second leg at Villa Park.
O'Neill had a premonition that Villa would face Rapid once more and is predicting a challenging tie.
“We had the feeling beforehand that we'd probably find ourselves drawn against Rapid Vienna again,” O'Neill (inset) told the club's official website, www.avfc.co.uk.
“As proved to be the case last year, this will be a difficult assignment against difficult opposition.
“But we are looking forward to the game and we will try to do our best to qualify for the group stage.
“This won't be easy because Rapid was as tough a draw as we could have encountered, but we'll be ready to go.”
Rapid manager Peter Pacult made his debut for Austria in October 1982 against O'Neill's Northern Ireland.
Manchester City should enjoy a comfortable passage into the group stage after drawing Romanian minnows Timisoara, who were only established in 2002 and finished fifth in their domestic league last season.
City manager boss Roberto Mancini is not expecting an easy ride, however.
“It will be a difficult game and any team from Romania will provide stiff opposition, particularly on their own ground,” he told the club's official website, www.mcfc.co.uk.
“We will look forward to both legs and obviously look to ensure we move to the group stages of the competition.”
Welsh Premier League outfit TNS must also travel for their first leg, heading to Bulgaria to meet CSKA Sofia.
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