Rafael Benitez has experienced the finest moment of his professional career as a coach in the UEFA Champions League but defeat for holders Inter Milan at home to unglamorous Dutch side FC Twente on Wednesday could bring him his lowest.
The 50-year-old has singularly failed so far to maintain Inter's remarkable form of last term under Jose Mourinho - who has little regard for Benitez and has gloated from afar at his discomfort - and the wise money is that anything but a win for Inter will see his tenure end after just months in the job. A Twente victory would even place Inter's chances of reaching the second round in jeopardy as they would go a point ahead of them with just one match remaining.
Group A leaders Spurs can seal their place in the second round in their first appearance in the Champions League with a home victory over struggling Bundesliga side Werder Bremen, whose own coach Thomas Schaaf is under increasing pressure with them having lost five of their last six matches.
Manchester United too can progress with a point away at Scottish side Rangers sufficient but their hosts need to beat the 2008 winners to have any hope of making the last 16 as second-placed Valencia are at home to pointless and goalless Turkish outfit Bursaspor. Valencia are presently two points ahead of Rangers.
Raul used to terrorise the Valencia defence in his days as a Real Madrid star but the veteran Spaniard will have his sites focussed on inflicting damage on France's semi-finalists last season Lyon and showed he is approaching his former level with a hat-trick for German side Schalke in their 4-0 humbling of Bremen on Saturday. Lyon still top Group B by two points from Schalke, though they missed a chance to seal their place in the last 16 with an away defeat to Benfica earlier this month and Raul will be keen to extend his record as Champions League all-time top goalscorer.
Benfica, who looked outstanding against Lyon before almost letting slip their 4-0 lead and ended up winning 4-3, can keep the pressure on the top two by beating hapless Israeli side Hapoel Tel-Aviv away.
Should 2009 champions Barcelona and Danish outsiders Copenhagen just draw against Panathinaikos - who have just hired a new coach in Portuguese Jesualdo Ferreira - and recently deposed Russian champions Rubin Kazan respectively they will take the two qualifying spots in Group D.
Benitez - who guided Liverpool to the 2005 Champions League trophy with an extraordinary comeback against AC Milan - accepts that Wednesday's match is hugely important coming on the back of a 2-1 defeat to Chievo on Sunday. Defeat left them sixth in Serie A and nine points off AC Milan at the top.
"I'm a professional with many years of experience and I know that I must simply prepare for the matches and that's it," said Benitez, who left the Liverpool post by mutual consent in June. "If we win on Wednesday, everything will change.
"We need to score goals to win games. On Wednesday we have an important match and we have to stick together. We're in trouble but we've got many players out injured and we have to manage this moment."
Spurs manager Harry Redknapp is keen to wrap up their place with a game to go but acknowledges that Werder Bremen may not be on form but they are still capable of pulling off a good result with the quality of players they have. "They're not a bad side, they're dangerous opposition and we need to put that one to bed if we can, get through this group."
Schaaf was kept in his post after the Bremen directors held two rounds of talks including with the players after the Schalke defeat which came soon after a 6-0 hammering by Stuttgart. Schaaf, though, appears lost as to what to do apart from stick to his already in place strategy. "There is no Plan B or C, we only have one and together we have to implement it better," said Schaaf.
The Rangers players would love to give manager Walter Smith something extra in his final season as their boss and nothing would be sweeter than beating United and somehow grabbing one of the two qualifying spots. Their in-form striker Kenny Miller, whose hat-trick saw them edge to a 3-2 away win at Kilmarnock in the domestic league accepts it will take a performance far above the ones they usually have to come up with domestically.
"It's going to be a tough night for us and we are going to have to ride our luck and play well and take our chances when they come along," said Miller, who has scored 18 times this season.