The way the Europa League draw was working out, it was inevitable that if Arsenal continued to progress they would be drawn-up against one of Europe's elite sides who also found themselves in Europe's secondary competition. As it turns-out, after limping by Ostersund on Thursday, Arsenal have been drawn against one of the most successful teams in European football for the Last 16 fixtures - AC Milan.

AC Milan's pedigree when it comes to European football is undeniable - they have 7 European Cups to their name - but the Italian giants have fallen on slightly harder times as of the past decade or so.

The side, currently managed by former player Gennaro Gattuso, have been a shadow of their former selves for a few years now. This season has not been much of an improvement - despite plentiful high-calibre additions in the transfer window, they currently sit in seventh place in Serie A, 25 points behind 1st placed Napoli.

Gattuso was promoted from his role with the Primavera youth team to take charge of the senior side until the end of the season after Vincenzo Montella was sacked in November.

The former Milan midfielder has overseen an upturn in fortunes, with the Italian outfit unbeaten in 11 matches across all competitions following Thursday's 1-0 victory over Ludogorets, which sealed a 4-0 aggregate win.

Like Arsenal, I Rossoneri find themselves unlikely to acquire a route back to the Champions League through the more traditional means of a top 4 league finish, and as such, have there sights firmly set on progressing by way of winning the Europa League.

With this being the case, you can be sure that Milan will be out for blood to make it to the quarter finals, and they will be bringing their considerable talent along with them to get the result they desire.

Milan is a team filled with big names - it always has been - and while these names may not be as intimidating as the likes of Kaka, Maldini and Shevchenko that graced Milan alongside Gattuso 10 years ago, they still possess plenty of players that any Premier League team would be delighted to have on their roster.

In terms of signings new to the team, Hakan Çalhanoğlu, André Silva, Franck Kessie and Ricardo Rodríguez all made the move to Milan for this season, and while there impact may not have been as large as initially wanted, they have started to make their presence more known as of late.

Perhaps, however, the most impressive of their signings was Leonardo Bonucci - the Italian defender made the move from Turin after playing an integral part in getting Juventus to the Champions League final last season, and is well-regarded as one of the best defender's in the world. Milan securing Bonucci's signature in the summer was somewhat an indicator of their intentions - they wanted to get back playing at the very highest level; and while it has not worked out as such thus far, they are a side that appear to be laying a foundation to make a return to their former glory.

Behind Bonucci and company will be goalkeeping wonderkid Gianluigi Donarumma, who is one of the most promising talents in any position at any club across the world. At just 18 years of age, the Italian has already amassed 93 caps for his club, as well as becoming the youngest player to ever feature for the Italian national side. Milan will want to be playing European football at the highest level to hold on to the young keeper, with every huge club in the world keeping an eye on Donnarumma's progress, and rightly so.

Seemingly unable to win against the teams higher than them in Serie A, they have seen a resurgence since the turn of the year that may bode well for Gattuso's future at the club. A win against the Gunners would be just what he needs to make a case for remaining in charge of the club past this season.

Milan have had a relatively easy time in the Europa League thus far - being drawn in a group with Austria Wien (2 wins), AEK Athens (2 nil-nil draws) and Croatian side Rijeka (who beat them in the final game of the group after having lost the first leg) - they finished on top of the group, and beat Ludogorets 4-0 on aggregate to get where they are.

In respect to the other clubs they've met along the way, Arsenal represent Milan's biggest test so far, and with the first leg being played at home for them, they'll be looking to make an impact across the first 90 minutes to enhance their chances of winning the fixture awaty from home.

It seems likely that leading the line for Arsenal against the Italians will be Danny Welbeck once more, with Pierre-Emerick Aubameyang cup-tied and Alexandre lacazette still expected to be recovering from injury. The English striker did not cover himself in glory over the two ties against Ostersund, contributing very little, so Milan will be optimistic of keeping him at bay - hopefully he can prove his deterrers wrong and put himself into contention to be part of the England 2018 world cup squad with good performances in a high-profile fixture.

With sides like RB Leipzig, Borussia Dortmund and Atletico Madrid all getting draws they will be optimistic about coming out as victors in - Zenit St Petersburg, FC Salzburg and Lokomotiv Moscow respectively - both Arsenal and Milan will be aware that games like theirs were always going to be necessary to come out trumps in this competition, with so many European heavyweights competing.

Once the League Cup final is completed, Wenger's side will have to seriously prepare themselves for the trip to Milan - a performance like Thursday's night will not be good enough to see them through to a good position in the second leg back in North London.

To end on a semi-optimistic note, while Gattuso's Milan will pose a big threat, they are a very beatable side, as has been the case on several occasions in Serie A this season. They won't be easily overturned, but of all the perceived AAA side's still competing in the Europa League, perhaps they were the best side to be matched with.

Arsenal will travel to the San Siro for the first leg of the Europa League Round of 16 knock-out fixtures against AC Milan, with the return leg coming up on the 15th of March back in the Emirates Stadium, with the winner progressing to the quarter finals of the competition.