Aston Villa have been drawn against Ajax and Hamburg in the group stages of the UEFA Cup.
Martin O'Neill's men are also up against Slavia Prague and Slovakian side MSK Zilina
Hamburg are managed by former West Brom player and Spurs boss Martin Jol and finished fourth in the Bundesliga last season.
Dutch giants Ajax finished as runners-up to PSV Eindhoven in the Eredivisie last season. They have won the Dutch championship 29 times, the European Cup four times, the UEFA Cup once and the European Cup Winners' Cup once.
Each team plays two matches at home and two away, with the top three teams from each group qualifying for the last 32.
Ajax visit Villa Park on October 23, with Martin O'Neill's men travelling to Slavia Prague on November 6.
Zilina then arrive in England on December 4, before Villa finish off the group with a trip to Hamburg on December 17.
O'Neill admitted he felt sorry for Jol, who was sacked by Tottenham last season.
The Villa boss told Sky Sports News: "I think that everybody would say on reflection it was pretty rough in the sense that they finished, twice, fifth and the looked as if they would be challenging.
"Anyone can get off to a poor start, as Tottenham have done this season. I have no doubt that they will recover from that, they are too good a squad not to do so, but it is good to see Martin doing very well."
Meanwhile, struggling Tottenham will face Spartak Moscow, Udinese, Dinamo Zagreb and NEC Nijmegen in the next stage of their UEFA Cup campaign.
Spurs are bottom of the Premier League after a miserable start to the season but they reached the group phase of the UEFA Cup with victory against Wisla Krakow over two legs.
Portsmouth were handed one of the most eye-catching match-ups by coming up against 2007 Champions League winners
AC Milan. Pompey were placed alongside the Italian giants in Group E with Heerenveen, Braga and Wolfsburg.
Manchester City will come up against former England manager Steve McClaren's FC Twente in Group A.
McClaren's side have already been beaten by Arsenal this season in a Champions League qualifier and will face another stiff test against Mark Hughes' men. Schalke, Paris St Germain and Racing Santander make up the group.
* UEFA CUP GROUP PHASE DRAW
GROUP A: Schalke, Paris St Germain, Manchester City, Racing Santander, FC Twente.
GROUP B: Benfica, Olympiacos, Galatasaray, Hertha Berlin, Metalist Kharkiv.
GROUP C: Sevilla, Stuttgart, Sampdoria, Partizan Belgrade, Standard Liege.
GROUP D: Tottenham, Spartak Moscow, Udinese, Dinamo Zagreb, NEC Nijmegen.
GROUP E: AC Milan, Heerenveen, Braga, Portsmouth, Wolfsburg.
GROUP F: Hamburg, Ajax, Slavia Prague, Aston Villa, MSK Zilina.
GROUP G: Valencia, Club Bruges, Rosenborg, FC Copenhagen, St Etienne.
GROUP H: CSKA Moscow, Deportivo La Coruna, Feyenoord, Nancy, Lech Poznan.
* Each team plays two matches at home and two away, with the top three teams from each group qualifying for the last 32.
* Ties to be played on October 23, November 6, November 27, December 3/4 and December 17/18.