LONDON, 22 November 2005 — The stakes are high for former European champions Manchester United, Porto and AC Milan in this week’s penultimate round of Champions League group matches.

All three are making heavy weather of reaching the last 16 with Porto facing certain elimination if they lose at home to Scottish champions Rangers in Group H tomorrow.

A loss for United at home to Villarreal today, combined with a victory for Lille over Benfica, will leave them scrapping for nothing more than a UEFA Cup place from Group D.

AC Milan face a testing night in Istanbul tomorrow against Fenerbahce where defeat would leave the six-time European champions struggling to emerge from a tight Group E.

Nerves are less fraught for some of Europe’s other big guns with holders Liverpool and Group G rivals Chelsea both set to book their places in the last 16 tomorrow.

Four clubs — Barcelona, Arsenal, Olympique Lyon and Real Madrid — have already qualified for the knockout phase.

Liverpool need just a point at home to Real Betis while English champions Chelsea will move through to the next round with victory over pointless Anderlecht.

Juventus and Bayern Munich can also take their places in the last 16 in home matches against Club Brugge and Rapid Vienna respectively in Group A. Juve need just a point while Bayern will go through with a victory as long as the Italians do not lose to Brugge.

Unsettled midfielder Michael Ballack is likely to miss Bayern’s clash against bottom club Rapid with a thigh injury suffered in Germany’s friendly against France.

Four-time winners Ajax are one Group B victory away from the knockout phase and should manage that against Sparta Prague, while Inter Milan need just a point against Artmedia Bratislava to emerge from Group H.

PSV Eindhoven are also in pole position in Group E and will clinch a top-two berth with victory at Schalke tomorrow, irrespective of how Milan fare against Fenerbahce.

Philip Cocu is doubtful after missing the weekend’s 4-4 draw at RKC Waalwijk while American DaMarcus Beasley is ruled out with a hamstring injury.

Porto, who were crowned champions of Europe under Jose Morinho in 2004, are desperate for a victory that would revive their flagging campaign.

Tomorrow’s Group F clash between group leaders Olympique Lyon and Real Madrid in the Bernabeu will give the Spanish club the perfect chance to erase the memory of Saturday’s 3-0 defeat by bitter rivals Barcelona at the Bernabeu. Madrid captain Raul will have to wait to become the first player to make 100 appearances in the Champions League since it began in 1992 after the striker was ruled out for around two months with a complex knee injury.

Raul suffered a partial tear of the cruciate ligament in his left knee against Barca and requires specialist treatment.