AC Milan leave behind the splendour of the San Siro for the more humble surroundings of Portsmouth's Fratton Park in the pick of Thursday's UEFA Cup action.
While Portsmouth entertain at home their Premier League rivals Manchester City and Tottenham are on the road at Schalke 04 and NEC Nijmegen respectively.
Portsmouth's first Group E game, and last under manager Harry Redknapp before his move to Spurs, resulted in a 3-0 loss at Sporting Braga.
For last season's FA Cup winners' second run-out in Europe it's now down to Redknapp's successor, Tony Adams, to plot the Italian superstars' downfall.
That promises to be no easy task given striker Jermain Defoe is nursing a calf injury to leave the attack spearheaded by Peter Crouch who has unfinished buiness with Milan.
The lanky attacker was part of the Liverpool side beaten by Milan in the 2007 Champions League final.
Man City will be praying their record Brazilian signing Robinho is fit for Schalke after coming off with an ankle injury in the second-half in the 3-0 win over Arsenal on Saturday.
Schalke lead Group A on four points with City a point behind in second with a game in hand after their 3-2 home success over Steve McClaren's FC Twente.
City's former Portsmouth striker Benjani believes the win over Arsenal was precisely the shot in the arm the team needed.
“We showed everyone that we are together and still going in the riht direction,” said the Zimbabwe international.
“It is no fun when you are not winning games. Having led against Chelsea and Liverpool at home we have finally beaten one of the big four and it will give us plenty of confidence.
“This week is very important and we couldn't have started it any better. We know that if we win in Schalke on Thursday night then we are close to making the knockout stages of the UEFA Cup and then there is the derby (against Manchester United) on Sunday.
“To win those two matches would be great and if we play like we did against Arsenal then there is no reason why we cannot have two more good results.”
Redknapp, takes his rejuvenated new charges Tottenham to Holland for their Group D date with Nijmegen.
Juande Ramos' replacement has conjured up a remarkable change in the fortunes of Spurs as evidenced by their 4-0 thrashing of Dynamo Zagreb last time out.
The Premier League side are placed second in the standings behind Udinese, who have the night off.
One of the players who has benefited from Redknapp's arrival is Croatia midfielder Luka Modric but he looks set to miss the match with a groin injury that kept him out of Sunday's 1-0 win over Blackburn.
Spurs' last trip to the Netherlands proved an unhappy occasion with PSV Eindhoven, then featuring Tottenham's goalkeeper Heurelho Gomes, knocking them out of last season's round of 16 on penalties.
In the other Group D tie Dynamo Zagreb take on Spartak Moscow under new management, with assistant Marijan Vlak stepping in to replace Branko Ivankovic who resigned as coach on Monday.
Another team going into battle with a new manager are Vfb Stuttgart who sacked Armin Veh at the weekend and appointed former Germany international Markus Babbel as his successor.
Former Liverpool and Bayern Munich defender Babbel takes charge for the first time in Stuttgart's Group C game at Sampdoria.
In Group G Saint Etienne will be grateful for some respite from the battering their receiving in the French league against Club Brugge.
Alain Perrin's bottom-of-the-table side are looking good for the next round after heading the standings with maximum points from their first two games.
The other French club on show Thursday are Paris Saint Germain who host Spaniards' Racing Santander on the back of Saturday's 1-0 upset of domestic champions Lyon.
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