Liverpool will face Anzhi Makhachkala, Udinese, and Young Boys in the Europa League group stage after the draw was made in Monaco on Friday.
Brendan Rodgers’ side, who edged to a narrow 2-1 aggregate victory over Hearts on Thursday night, were placed in a testing Group A which will see the Reds meet former Intertoto Cup winners Udinese.
The Merseysiders, who are three-time winners of the competition, will also face Young Boys, the Swiss side who beat Tottenham 3-0 in the home leg of their Champions League play-off in 2010.
But perhaps the most difficult test for the Northern Irishman in his debut campaign in Europe will come against cash-rich Russian outfit Anzhi Makhachkala, who boast prolific goal scorer Samuel Eto’o.
Tottenham’s toughest assignment of the group-stage should come against the 1998 finalists Lazio, while a trip to Panathinaikos will also be demanding, with Slovenia’s NK Maribor completing Group J.
Alan Pardew’s Newcastle United, who eased to a 2-1 aggregate win against Atromitos at St James’ Park on Thursday night, will take on 1996 runners-up Bourdeaux.
The current Magpies squad will be looking to better Bobby Robson’s side who were beaten semi-finalists in 2004, and reach the Europa League final in Amsterdam next May.
And Pardew will be quietly optimistic about getting results against their other Group D opponents, Club Brugge and Portugal’s Marito.
Finally, defending champions Atletico Madrid were handed a relatively kind draw, with Diego Simeone’s side set to face Hapoel Tel-Aviv, Plzen and Academica in Group B.
Europa League group stage draw in full:
Group A: LIVERPOOL, Udinese, Young Boys, Anzhi Makhachkala.
Group B: Atletico Madrid, Hapoel Tel-Aviv, Plzen, Academica.
Group C: Marseille, Fenerbache, Borussia Monchengladbach, AEL.
Group D: Bourdeaux, Club Brugge, NEWCASTLE UNITED, Maritimo.
Group E: Stuttgart, Copenhagen, Steaua Bucharest, Molde.
Group F: PSV Eindhoven, Napoli, Dnipro Dnipropetrovsk, AIK.
Group G: Sporting Lisbon, Basel, Genk, Videoton.
Group H: Internazionale, Rubin Kazan, Partizan, Nefti.
Group I: Lyon, Athletic Bilbao, Sparta Praha, Hapoel Kiryat Shmona.
Group J: TOTTENHAM HOTSPUR, Panathinaikos, Lazio, NK Maribor.
Group K: Bayer Leverkusen, Metalist Kharkiv, Rosenborg, Rapid Wien.
Group L: Twente, Hannover 96, Levante, Helsingborg.