After four successive Round of 16 defeats, Arsenal host Monaco on Wednesday looking to take a major step toward finally returning to the quarterfinals. Finalists in 2006 and semifinalists three years later, Arsenal have been punished heavily in recent years for finishing runners-up in the group phase.

Faced with ties against European powers Barcelona, Milan and twice Bayern Munich in the first knockout round, Arsenal’s exits have been swift. This season, there was again disappointment in finishing second, especially after collapsing to drop two crucial points at home to Anderlecht. But fortune finally smiled on them in December’s draw.

Monaco were by almost all reckonings the weakest of the group winners. They finished with the lowest points total, 11, and incredibly scored just four goals in six matches against Bayer Leverkusen, Zenit St Petersburg and Benfica. A year or so ago the tie would have had a very different feel. An incredible splurge of investment by Russian billionaire owner Dmitry Rybolovlev followed their promotion to Ligue Un in 2013, with the goal of quickly turning them into a major European force. Eyebrows were raised as established stars like Radamel Falcao, James Rodriguez and Joao Moutinho arrived, helping Monaco to second in the France and getting a coveted place in the Champions League. But then came a just as drastic change in direction.

Claiming that the focus was now going to be on more measured progress and a need to comply with UEFA’s Financial Fair Play regulations, although with rumors that it had more to do with the owner’s costly divorce settlement, the crown jewels were sold off. James left for Real Madrid and Falcao, initially on loan, was shipped off to Manchester United. And after manager Claudio Ranieri left, Portuguese Leonardo Jardim was a surprise choice as his replacement. Three defeats in their first five league games suggested his stay may not be a long one and that this was a club ready to fall almost as fast as it had ascended.

Yet the ship has been steadied considerably since and they now lie fourth in Ligue Un. As their Champions League record suggested, that form has been built on defensive solidity. Indeed, they have remarkably conceded just three goals in 17 matches in all competitions since the beginning of December.  That they are far from free-flowing is evidenced in the fact that they have scored just 21 goals in that time. Without Falcao, Dimitar Berbatov is their top scorer with just seven goals in all competitions.

The former Manchester United and Tottenham striker will certainly have ample motivation to add to that tally against Arsenal, and Monaco’s defensive record means that conceding an away goal could be particularly costly to the Premier League side in the first leg at the Emirates Stadium. While the matchup represents a golden chance for Arsenal to return to the Champions League’s latter stages, complacency and a lack of focus has the potential to leave Arsene Wenger’s men facing an uphill struggle heading back to a city he used to call home in three weeks’ time.

Wenger made his name at Monaco, coaching them for seven years before being painfully sacked in 1994. It was with the club in the principality that Wenger first developed a reputation as being one of the game’s innovators with regards to statistics and fitness. It is an image that has taken some denting in recent years as Arsenal have endured a more-than-decade-long wait for a Premier League title amid Wenger seeming increasingly unwilling to compromise his principals.

But highlighted by a first victory in some time away at a top team, against Manchester City last month, Arsenal have developed greater tactical flexibility of late. That change has played a big part in Arsenal winning eight of their last nine matches and rising back into the Champions League places, and will likely need to continue if Arsenal are to go further in this season’s competition.

Prediction: Arsenal 1-0 Monaco

Team News

Arsenal: Alex Oxlade-Chamberlain is likely to remain sidelined, alongside Aaron Ramsey, Mikel Arteta and Mathieu Debuchy.

Monaco: Left-back Layvin Kurzawa and winger Yannick Ferreira-Carrasco are doubts, although only have minor issues. But Monaco will be without the suspended midfielder Jérémy  Toulalan, former Chelsea and Real Madrid defender Ricardo Carvalho as well as Tiemoué Bakayoko and Andrea Raggi.