Europa League last 16: Seven things to look out for with Man United, Arsenal and Tottenham in action

The Europa League knockout stages kick off in earnest tonight, just two weeks after the last-32 whittled down the competition to 16 sides.

Four British teams remain, with Manchester United facing AC Milan in a clash of European giants, Arsenal out for revenge against Olympiacos, Spurs facing Dinamo Zagreb and Rangers hoping to follow up their title-winning party in style.

Elsewhere Unai Emery is looking to add to his impressive Europa League trophy haul with Villarreal while Roma coach Paulo Fonseca will hope the law of the ex doesn’t strike against his former side Shakhtar Donetsk.

Manchester United and Milan’s last-16 tie would not look out of place in the Champions League

Arsenal are out for revenge after heartache against Olympiacos in last year's round of 32

Arsenal are out for revenge after heartache against Olympiacos in last year’s round of 32

Here, Sportsmail looks at the main talking points ahead of tonight’s last-16 first legs.

Man United and Milan’s heavyweight clash  

It’s a tie that wouldn’t look out of place in the Champions League, but Man United and Milan’s meeting in the Europa League demonstrates how both European giants have lost their way in the past decade.

In fact, the last time these two sides played each other was in the last-16 of Europe’s premier club competition in 2010. Wayne Rooney scored twice before Park Ji-Sung and Darren Fletcher wrapped up a 4-0 win on the night and an aggregate 7-2 victory to send Sir Alex Ferguson’s men into the quarter-finals.

United briefly flirted with a title challenge this season and beat Man City 2-0 at the weekend

United briefly flirted with a title challenge this season and beat Man City 2-0 at the weekend

Zlatan Ibrahimovic has been in fine form for Milan but may miss the first leg due to injury

Zlatan Ibrahimovic has been in fine form for Milan but may miss the first leg due to injury

United have failed to consistently reach those heights since Ferguson’s retirement in 2013, while Milan finished as low as 10th in Serie A in 2014-15 and were even banned from Europe for a year for breaching Financial Fair Play rules in 2019.

Both seem to be getting back to winning ways. Under Ole Gunnar Solskjaer, the Red Devils finally have some stability and briefly flirted with a title challenge this season before Man City pulled clear.

Meanwhile, the Rossoneri are still just about in the running for their first Scudetto in 10 years thanks to a born-again Zlatan Ibrahimovic, even if they now trail leaders Inter by six points.

Ibrahimovic looked like he might miss the first leg against his former club with a muscular injury but manager Stefano Pioli is hopeful he will play. The Swedish striker’s presence would only add to the sense of occasion.

Arsenal out for revenge against Olympiacos 

Arsenal’s tie against Olympiacos should tell us a lot about the Gunners’ title aspirations after they survived a scare against Benfica to get through the last-32.

Last year Pierre-Emerick Aubameyang missed a gilt-edged chance late on against the Greek side as Arsenal were knocked out of the round of 32 on away goals.

That defeat will surely weigh on the minds of Mikel Arteta’s players after Aubameyang admitted he was thinking about his miss when he nodded home the winner against Benfica.

Arsenal's shock last-32 defeat to Olympiacos last year has not been forgotten by players

Arsenal’s shock last-32 defeat to Olympiacos last year has not been forgotten by players

‘I think everybody is happy tonight and definitely I had this in my head,’ he told BT Sport when asked about the miss against Olympiacos.

‘But this gives me power every day to take the error from the past and transform it into strength.’ 

Arsenal will hope to take similar strength into their last-16 clash, but they must be wary of an Olympiacos side who are unbeaten in their last 10 matches at the Karaiskasis Stadium – the same venue where Arteta’s men edged out Benfica.

Gareth Bale’s renaissance at Spurs  

It was only last month that Bale’s agent Jonathan Barnett was claiming the Welshman was winding down his career after a string of disappointing performances for Spurs.

But six goals in Bale’s last six appearances, including two goals and an assist to help Spurs past Wolfsberger in the last-32, would suggest otherwise.

He was similarly brilliant in the 4-1 defeat of Crystal Palace on Sunday as he combined with Harry Kane to devastating effect, grabbing two goals and reminding fans why they were so excited to see him back in north London last summer.

By now it is clear that Bale is a different player to the one that left for Real Madrid in 2013, but that doesn’t matter. He still has the ability to dazzle, and Dinamo Zagreb should be very afraid if he gets on the field.  

Steven Gerrard looking to do what Brendan Rodgers couldn’t

It’s fair to say the Europa League probably hasn’t been the first thing on Gerrard’s mind since his Rangers side became Scottish champions for the first time in 10 years.

Celtic’s 0-0 draw with Dundee United on Sunday confirmed that colossal achievement and Rangers players and fans have been celebrating since. 

Rangers fans and players have been celebrating their first Scottish Premiership win in 10 years

Rangers fans and players have been celebrating their first Scottish Premiership win in 10 years

Gerrard insists they are ‘back in the routine’ ahead of their last-16 game against Slavia Prague, where they will look to harness the energy of those title celebrations on the pitch.

The Liverpool legend will be well aware of what Rangers’ next opponents can do after his old boss Rodgers and Leicester City were dumped out of the competition by the Czechs’ 2-0 victory in the last-32 second leg. 

Rangers showed their firepower in defeating Antwerp 9-5 on aggregate in the last round and Gerrard will want more of the same as they look to improve on an already special season.

Unai Emery in the hunt for another Europa League trophy

With three titles to his name, only Giovanni Trapattoni can claim to have the same hold on the Europa League – or UEFA Cup as it was once known – as Unai Emery. 

What makes Emery’s record even more impressive is the fact all three trophies came with one club in Sevilla, the masters of this competition. 

The Spaniard has endured difficult spells at Paris Saint-Germain and Arsenal since leaving Andalusia and now finds himself back in Spain with Villarreal. 

Unai Emery (left) is looking for a record fourth Europa League trophy with his side Villarreal

Unai Emery (left) is looking for a record fourth Europa League trophy with his side Villarreal

The Yellow Submarine looked to be mounting a top four challenge before their form dropped off – Emery’s side are seventh in LaLiga with a remarkable 13 draws this season – but they have won all but one of their eight Europa League games so far.

It is no surprise that Emery is taking strength from his favoured tournament again. Villarreal were excellent against Red Bull Salzburg in the last-32 and may give their manager yet another triumph if they can get past Dynamo Kyiv.

Paulo Fonseca faces another former employer     

‘I’m certain this is going to be a difficult match,’ said Roma manager Fonseca of his side’s last-16 meeting with Shakhtar. ‘I don’t like to face my former teams.’

Fonseca’s apprehension is understandable. After beating a former employer in Braga in the round of 32, he would have hoped to avoid another awkward encounter with a team from his past. 

Instead Roma were drawn with Shakhtar, the club where Fonseca won the Ukrainian Premier League and Cup double three years in a row and almost gave the Giallorossi themselves a shock in the Champions League last-16.

The Serie A side have six wins in their last seven games but Shakhtar will represent a stern test after stunning Real Madrid home and away in the Champions League earlier this season.

Granada look to continue their European fairytale  

Granada’s journey in their first season of European football has been remarkable. 

Diego Martinez’s side had to see off Teuta, Locomotive Tbilisi and Malmo to even make it into the group stage. They came second in their group, beating former European Cup winners PSV Eindhoven along the way.

But their greatest heroics came in the last-32 against Napoli, where few gave them a chance of progressing. Yangel Herrera and Kenedy gave them a 2-0 lead in the first leg, before goalkeeper Rui Silva and his defence ensured they held on at the Stadio Diego Armando Maradona to advance with a narrow 2-1 defeat.  

Regardless of what happens next against Molde, to even get this far is a huge achievement for Granada. 

Granada are looking to continue their European fairytale after beating Napoli in the last-32

Granada are looking to continue their European fairytale after beating Napoli in the last-32