Liverpool will begin its Europa League campaign at home to Rabotnicki of Macedonia or Armenian club Mika in the third qualifying round.
Italy's Juventus, the other traditional power in Friday's draw, was paired away to Ireland's Shamrock Rovers or Bnei Yehuda of Israel, who complete a second qualifying round tie next week after drawing 1-1 in the first leg.
Both storied teams - who have been champions of Europe a combined seven times - finished seventh in their domestic leagues last season, failing to qualify for the Champions League.
For five-time European champion Liverpool, which parted with coach Rafa Benitez in May, a July 29 start in the second-tier competition represents a fall from grace.
Liverpool will have to advance without Fernando Torres, Pepe Reina, Dirk Kuyt and Ryan Babel, who are all being allowed to rest after being part of the Spain and Netherlands squads that reached the World Cup final on Sunday.
''It is every bit as difficult as I was expecting,'' new Liverpool manager Roy Hodgson said. At this stage of the qualifying round there are a lot of teams from countries you don't know too well and teams who probably will not make it to the latter stages of the competition.
''I know Rabotnicki are in Europe every year but I don't know much about Mika, although I know Armenia having been there as Finland manager.''
The first leg at Anfield will be Hodgson's first competitive match in charge of Liverpool. He led Fulham to the Europa League final in May - a 2-1 extra-time loss to Atletico Madrid.
Liverpool's possible opponents will remain a mystery until Thursday, when Rabotnicki travels to Armenia with a 1-0 lead in its second qualifying round match.
''We know we will get two tough games and it is up to us to get as much information as we can in the limited period of time we have,'' Hodgson said.
Liverpool and Juventus are also three-time winners of the UEFA Cup, the second-tier competition that was rebranded as the Europa League last year.
Juventus' potential opponents - Bnei Yehuda of Tel Aviv and Shamrock Rovers - are poised at 1-1 going into next week's second leg.
''I don't know whether it is better to go to the cool weather in Ireland or the heat in Israel,'' Juventus striker Alessandro Del Piero said. ''What I know is that we must absolutely make it through to the next round.''
Red Star Belgrade, the 1991 European champion, also featured in Friday's draw, and will play at home first against Slovakia's Slovan Bratislava.
Turkey's Galatasaray, the 2000 UEFA Cup winner, was drawn at home to OFK Belgrade from Serbia or Torpedo Zhodino from Belarus.
IFK Gothenburg of Sweden, a two-time UEFA Cup winner in the 1980s, is away to AZ Alkmaar of the Netherlands.
First-leg matches are played July 29 and returns on Aug. 5.
The winners advance to the playoff round before progressing to the group stage.
The complex competition structure has eight teams who finish third in their Champions League groups in December join the Europa League knockout rounds in February.
