Benfica v Rangers in Europa League - World Cup winners and rising stars await in Lisbon

When you think of Benfica, you think of Eusebio.

The jewel in the crown of his career with Benfica was the European Cup winners' medal he won at the end of his first season there, scoring twice in their final victory over Real Madrid in Amsterdam.

Although he played in three more finals in the tournament, a second success eluded him - but his incredible haul of 473 goals in 440 appearances will surely never be beaten.

Legend has it that Eusebio had a soft spot for Rangers after meeting and going on to become firm friends with Ibrox legend Willie Henderson.

The pair met in 1964 as part of a 'Rest of the World' select for a friendly in Denmark and were close up until Eusebio's death just over a decade ago.

• Inside the £1bn Benfica talent factory Rangers will face

Like Eusebio's hat-trick of final defeats, Henderson had his own European heartache. He lost in the 1967 Cup Winners' Cup final to Bayern Munich, and left the club just before they got their hands on the trophy in 1972.

Now, in 2024, the sides meet for a place in the quarter-finals of the Europa League in what is their most high-profile meeting so far.

They drew twice in the group stage during the 2020-21 season, when games were played behind closed doors, with Rangers blowing two-goal leads in both matches.

But with the Europa League's Dublin showpiece just three rounds away, the stakes are higher this time around.

The reigning and 38-time Portuguese champions come into the tie having lost back-to-back matches for the first time this season. They exited the Taca de Portugal, their national cup competition, at the hands of bitter city rivals Sporting before being humbled when Porto thrashed them 5-0 in 'O Classico'.

The latter was just their second Primeira Liga defeat of the season - and the first since the opening day of the campaign when they lost to Boavista.

Head coach Roger Schmidt has come in for intense criticism in the aftermath, not just for his team's capitulation but for his refusal to apologise to supporters.

Despite that, there is little doubt this is a huge challenge for Philippe Clement's Rangers side as they also look to bounce back from a first defeat of the calendar year.

The draw certainly wasn't terribly kind to Clement, given they were seeded. The likes of Qarabag of Azerbaijan or Freiburg - who sit mid-table in the German Bundesliga with one win in eight games - would surely have been easier opponents.

And despite their very recent ills, the Lisbon side boast two World Cup winners and some of European football's most promising talent in their squad.

Veterans Nicolas Otamendi and Angel di Maria helped Argentina to glory in Qatar in 2022 and while they were all overshadowed by the Lionel Messi story, both were key to that success.

Benfica skipper Otamendi, the former Manchester City defender, won his 100th cap in the final against France, while ex-Manchester United winger Di Maria - who arrived from Juventus last summer - scored Argentina's second that day and continues to find the net on a regular basis.

His 14 goals this season - including the brace that gave Benfica their Europa League play-off round win over Toulouse - make him second only to Rafa Silva in the side's scoring chart.

Silva, along with Otamendi, are the only players still at Benfica from their previous tussles with Rangers.

At the other end of the career-span are a host of players who will likely make big waves in the years to come.

Otamendi's centre-back partner Antonio Silva is only 20 but has already played for Portugal seven times and big-spenders Chelsea and Manchester United are reportedly among his suitors.

Fellow academy graduate Joao Neves, a multi-talented defensive midfielder, is just 19 and has also broken into the senior national side.

Turkish midfielder Orkun Kokcu joined for about £25m from Feyenoord in pre-season in what was a record transfer fee paid by Benfica.

There are other youngsters knocking on the first team door but it remains Silva who could be the biggest threat to Rangers' progression. He scored against Steven Gerrard's team in the Lisbon meeting and has amassed 17 goals this season - including two in their Champions League group.

While always in the shadow of the great Eusebio, whose statue stands outside their iconic stadium, Benfica have big ambitions on the continent this season as they aim to end a 62-year wait for a European trophy.

They hope to continue that journey against Rangers in this mouthwatering last-16 tie.

• Visit our Rangers page for all the latest news, analysis and fan views
• You can now get Rangers news notifications in the BBC Sport app - find out more

• Our coverage of Rangers is bigger and better than ever before - here's everything you need to know to make sure you never miss a moment
• Everything Rangers - go straight to all the best content