Two-time UEFA Champions League-winning coaches Jose Mourinho and Carlo Ancelotti will be looking to guide Real Madrid and Paris Saint Germain respectively to a second successive victory in the group stages on Wednesday.
Both Mourinho and then Ancelotti failed to deliver European club football's premier trophy with Chelsea - galling for both that the relative novice Roberto Di Matteo succeeded where they failed last season.
The pressure is very much on both men this time round as Mourinho, who has won with Porto and Inter Milan, has yet to deliver the trophy to Real - they have gone out in the semi-finals in the past two seasons.
Ancelotti, twice a winner with AC Milan, might be in his first Champions League campaign with the French side but their Qatari backers will be expecting a long run in the competition after laying out millions on players.
Both have tricky away trips Real to Dutch giants Ajax and PSG to Porto.
While Real grabbed a late but deserved 3-2 victory at home to Manchester City in the first game, Ajax fell to a late goal away at Borussia Dortmund.
Since the victory over City Real have looked a different side to the one that had fallen eight points behind bitter rivals Barcelona in La Liga, and while the gap remains the same Los Meringues have won both their subsequent league games, thrashing Deportivo La Coruna 5-1 on Sunday.
Mourinho will have to juggle his line-up as it is a crucial week with a trip to Barcelona coming this weekend where defeat would dim their hopes of retaining their title after just seven games of the season.
The Portuguese handler, however, is not willing to choose a second string team against Ajax despite having beaten them in all four of their most recent Champions League encounters and not conceding a goal.
"Ajax are constantly having to rebuild their side but always seem to find new and interesting players, men who want to make a name for themselves and fight for the cause," said the 49-year-old.
Pivotal match for PSG
Ancelotti also has a key match to look forward to at the weekend, Sunday's always high-octane trip to historical rivals Marseille and with the chance of leapfrogging them at the top of the table if they win there.
However, the Italian has been at pains to keep his players minds focussed on the Porto game especially as they like PSG won their opening game, the Portuguese side beating Dinamo Zagreb 2-0 away while PSG thrashed Dynamo Kiev 4-1.
"This is a crucial match for us in terms of the Champions League group," said Ancelotti.
"If we win then we are in pole position to progress as one of the top two and further down the line it may allow me to rotate the squad a bit more."
Ancelotti's former side AC Milan would kill for three points on Wednesday away at Zenit St Petersburg to alleviate both the pressure on coach Massimiliano Allegri and give them some much needed impetus in what has been a desperately disappointing start to the season.
Milan opened their campaign with a disappointing 0-0 draw at home to Anderlecht while Zenit fared worse losing 3-0 away at Malaga.
It hasn't helped Allegri that Ancelotti and PSG took away two of their most impressive performers, Zlatan Ibrahimovic and Thiago Silva, in multi-million euro deals but those excuses are wearing thin.
The one consolation for Allegri is that Zenit are in a worse state, as the big money signings of Hulk and Belgian midfielder Axel Witsel, instead of boosting the squad, have sparked deep unrest which the Italian side will be hoping they can benefit from on Wednesday.