Middlesbrough will face last season's semi-finalists AZ Alkmaar in Group D, and are also up against Ukrainian side Dniepropetrovsk, who hammered Hibernian 5-1 on aggregate in the first round, Swiss side Grasshopper Zurich and Litex Lovech of Bulgaria.

Turkish side Besiktas are the top side in Bolton's group H which also includes Spanish side Sevilla, Russia's Zenit St. Petersburg and Vitoria Guimaraes of Portugal.

Bolton manager Sam Allardyce said: "We are in an excellent group with some very good sides who will make it difficult for us.

"At this level all matches will be hard but we are here on merit and we look forward to seeing where we might be travelling in Europe."

UEFA Cup holders CSKA Moscow have drawn French side Marseille in Group F, Dutch outfit Heerenveen and Bulgarian's Levski Sofia and Dinamo Bucharest of Romania.

Marseille president Pape Diouf remains confident of his side progressing.

"It's a very evenly balanced draw without anyone spectacular. But we're up against the title-holders all the same. But we have our chances of qualifying if we give it everything," said Diouf.

New Monaco coach Francesco Guidolin will be hoping to make his mark for his side who are favourites in group A.

The French play Czech side Slavia Prague, and in-form German outfit Hamburg, who are unbeaten so far this season in the Bundesliga. CSKA Sofia and Norwegian club Viking FK complete the group.

In the group phase, each club plays two matches at home and two away on October 20, November 3, November 24, November 30 or December 1 and December 14 or 15.

The top three teams from each group qualifies for the knockout phase which will also inlude the eight teams who finish third in their Champions League group.