Besiktas wait for Bolton as Boro face tough Dutch test

Sam Allardyce's side have been drawn in Group H with the Istanbul club, Russia's Zenit St Petersburg, Vitoria Guimaraes of Portugal - their other away fixture - and Seville of Spain.

Middlesbrough face a difficult trip to the Netherlands to take on last season's Uefa Cup semi-finalists AZ Alkmaar in Group D. Boro begin with a trip to Zurich to play Grasshoppers before facing the Ukrainian side Dnipro Dniprope- trovsk at the Riverside on 3 November. They take on the Dutch side in the third match before finishing at home at home to Bulgarian club Litex Lovech on 15 December.

The Bolton chairman, Phil Gartside, predicted a difficult task ahead for Wanderers. "If we're going to progress, we'll have to play at our best," he said. "You want some exciting away trips to experience more European football and some good matches at home so you can face the likes of Sevilla."

"I think we're lucky because we don't have to tell the players about European football - most of them have already been there."

The Middlesbrough manager, Steve McClaren, vowed to do his homework as he plots his side's progression to the knock-out stage of the tournament.

The trip to the Netherlands on 24 November to meet Louis van Gaal's Alkmaar, currently top of the Dutch league, could prove their toughest test, and McClaren is well aware of the threat they will pose.

He saw Alkmaar at close hand at the end of last season while looking at the Sporting Lisbon pair Fabio Rochemback and Roudolph Douala as the Portuguese side edged past the Dutch team to reach the Uefa Cup final on away goals.

"They are an attack-minded team and are top of the Dutch league and going great," McClaren said. "They have got a talented manager and some very good players."

Boro will prepare detailed dossiers on all their opponents as they attempt to improve upon their first ever European adventure, which took them to the last 16, where they too lost to Sporting. "Grasshoppers have got a strong reputation in European football and they are currently doing well in their league, as always," McClaren said.

At the draw in Nyon, Switerland, yesterday the 40 clubs were split into eight groups of five with three teams from each to advance to the next round. The competition then reverts to a knockout stage and the 24 winners will be joined by the eight third-place finishers from the Champions' League group phase.

Defending champions CSKA Moscow, will play Marseille, one of five French clubs in the draw, in the group stage. The draw kept teams from the same federations apart, which means that France could have at least five teams in the next round.

Uefa Cup group stage draw

MIDDLESBROUGH Group D

20 October v Grasshoppers (Switzerland, away)

3 November v Dnipro Dnipropetrovsk (Ukraine, home)

24 November v AZ Alkmaar (Neth, away)

15 December v Litex Lovech (Bulgaria, home)

BOLTON Group H

20 October v Besiktas (Turkey, away)

3 November v Zenit St Petersburg (Russia, home)

24 November v Vitoria Guimaraes (Portugal, away)

15 December v Seville (Spain, home)