Pep Guardiola faces a mammoth test if he is to keep alive his hopes of ending his time in charge of Bayern Munich with a Champions League title. On Tuesday, Bayern visit last season’s runners-up Juventus in the first leg of what is surely the pick of the Champions League Round-of-16 matchups.

What was already a difficult prospect when the draw was made in December, has only become more so in the intervening two months. Just months after only a defeat to Barcelona in the Champions League final last May prevented them from landing a treble, Juventus had endured their worst start to a Serie A season for more than a century. Having lost a trio of hugely influential players in Andrea Pirlo, Carlos Tevez and, to Bayern, Arturo Vidal, it appeared the Bianconeri were set for a season of transition.

That transition has proved to be a far quicker process, however. Led by the goals and skills of one of the new generation of talent brought in to replace the departed veterans last summer, Paulo Dybala, Juventus went on a 15-match win streak in Serie A to surge back to the top of the table. Despite that run coming to an end with a goalless draw at Bologna on Saturday, Massimiliano Allegri’s side are suddenly favorites once again to land a fifth consecutive Scudetto.

Meanwhile, things have not run so smoothly at Bayern. Guardiola’s first two seasons in charge resulted in Bundesliga titles but disappointment in the Champions League as his team faded down the stretch and were besieged by injury problems. And those fitness issues have reared their head once more as the season enters its crucial period.

This time around, rather than a crippling list of injuries to his attacking talent, it is his defense that has been hit hard. Indeed, Bayern’s four leading center-backs have all been impacted. Jerome Boateng, Javi Martínez  and Holger Badstuber are definitely ruled out, while Mehdi Benatia, although back in training, looks unlikely to be thrown straight into the starting lineup having not featured in over two months.

It is the last thing Guardiola will have wanted as he seeks to end his time in Bavaria on a high. Since the draw as made, of course, it has also been confirmed not only that the Catalan will leave Bayern Munich at the end of the campaign but that he will take up residence at Manchester City from next season.

Keeping his squad motivated when they know the man in charge has chosen to move elsewhere is now a major challenge. And he will surely be keen to ensure his legacy at the German giants. Currently eight points clear at the top, Bayern look set to make it three straight Bundesliga titles under his charge. But there is a sense that he is still far from universally loved. A sign held up at the Allianz Arena reading “Pep was never our thing anyway,” only reinforced that disconnect.

To an extent, Guardiola has always been haunted by the fact that he took over a Bayern team that had just won the treble under Jupp Heynckes. Anything less than a Champions League title will be seen by many as a failure, despite the magnificent style with which his team has performed over the course of three years.

But a tie with Juventus can perhaps be the spark for Guardiola to match Heynckes’ achievements of bowing out in a blaze of glory. The last meeting between the two European giants came in Bayern’s 2012 Champions League winning campaign, when they beat the Italian champions 2-0 home and away.

There remains plenty to encourage Guardiola. For all his defensive problems, his attacking weapons are close to being at full potency, with Franck Ribery making his first home outing in close to a year in a 3-1 win over Darmstadt on Saturday. The game also featured two goals, one a spectacular effort, from Thomas Müller and another from Robert Lewandowski to take the forward duo’s tally to 56 for the season in all competitions.

It was Lewandowski’s arrival in the summer of 2014 that brought about the acrimonious exit of Mario Mandzukic. And now, having found his way to Juventus via Atlético Madrid, the Croatia international will surely be looking to make a point to Guardiola at the Juventus Stadium on Tuesday.

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Allegri will be missing defender Martín Cáceres and left-sided players Alex Sandro and Kwadwo Asamoah.

Bayern Munich: With Boateng, Martínez  and Badstuber out, January loan signing from Spartak Moscow Serdar Tasci could feature, having made his debut at the weekend. However, with Tasci at fault for the Darmstadt goal, Guardiola may opt for a makeshift center-back pairing of David Alaba and Joshua Kimmich.

Prediction: Juventus have been phenomenally strong at home under Allegri. This season they have only suffered one defeat in all competitions at their own stadium, and that was back in August. In the 16 game since then, they have won on all but three occasions. In last season’s Champions League they won each of their home games in the knockout phase, against Borussia Dortmund, Monaco and Real Madrid. Bayern Munich, meanwhile, have a surprisingly poor recent record on the road in Europe, losing four and winning just two of their last seven Champions League games away from the Allianz Arena. Given Bayern’s defensive problems and Juventus’ fine form, the Italians may grab a lead to take to Bavaria in three weeks’ time.

Predicted score: Juventus 2-1 Bayern Munich