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Juventus and Milan Face Tough Europa League Challenges

The velvet backdrop of Montecarlo delivered little comfort for Italy’s only Europa League representatives. Juventus and Milan walked away from the 2026-27 league-phase draw with routes that are rich in intrigue, heavy on travel, and light on guarantees.

Both clubs, bruised by a Serie A campaign that left them fifth and sixth respectively, now carry the weight of Italian expectations into a competition that begins on September 16/17 and runs through to January 28, 2027.

Juventus: Tradition meets turbulence

Luciano Spalletti’s face in Frosinone last weekend told its own story. A dejected figure on the touchline as Juventus laboured through their Serie A opener, he now stares at a Europa League schedule that will test both depth and resolve.

The Bianconeri’s league-phase slate is anything but gentle:

  • Real Sociedad (H)
  • AZ Alkmaar (A)
  • Rennes (H)
  • Ferencváros (A)
  • Omonia (H)
  • Celta Vigo (A)
  • NEC (H)
  • Hapoel Beer Sheva (A)

It is a mix of technical, high-tempo opponents and awkward away days. Real Sociedad at home brings immediate European edge, a meeting with a side comfortable on the ball and unafraid of big stages. AZ Alkmaar away is the kind of Dutch assignment that punishes any defensive hesitation. Rennes, with their athleticism and intensity, will not allow Juventus to drift through ninety minutes in Turin.

Then come the trips that define Europa League campaigns. Ferencváros in Budapest, Celta Vigo in Spain, Hapoel Beer Sheva in Israel: long flights, hostile atmospheres, and little margin for error. Omonia and NEC, on paper, look more manageable, but this format rarely forgives complacency.

For a club that once measured itself only by Champions League standards, this competition now becomes a proving ground. The new Europa League structure is ruthless: only the top eight in the overall table go straight to the Round of 16. Those from eighth to 24th are thrown into a knock-out play-off. Anything lower than that, and the journey ends early.

Juventus cannot afford a slow start. Not this time.

Milan: Glamour ties and English grit

On the other side of northern Italy, Ruben Amorim faces a very different kind of challenge. Milan’s draw offers glamour, nostalgia, and a sharp Premier League edge.

The Rossoneri’s opponents:

  • Benfica (H)
  • Olympiacos (A)
  • Ferencváros (H)
  • Salzburg (A)
  • Sunderland (H)
  • Bournemouth (A)
  • Ararat (H)
  • Levski Sofia (A)

Benfica at San Siro jumps off the page. Two clubs steeped in European history, now colliding in a competition both feel they should be using as a springboard back to the elite. Olympiacos away, in Piraeus, is a furnace of noise and colour, the sort of night that exposes any tactical uncertainty.

Salzburg bring energy and youth, a team that runs relentlessly and presses high. Ferencváros, this time in Milan, provide a link between the two Italian campaigns, a shared opponent that may offer a quiet benchmark of where each Serie A side really stands.

Then come the English tests. Sunderland at home, Bournemouth away. Different profiles, same warning. English sides in Europe, regardless of status, arrive with intensity and physicality. Bournemouth on the south coast will not be a pleasant excursion for a Milan side still adapting to Amorim’s demands.

Ararat and Levski Sofia round out the group of opponents, fixtures that, on reputation alone, Milan will be expected to control. But the new league phase is about accumulation. Points, goal difference, momentum. Slip in one of those supposedly “lighter” matches and the entire seeding picture can twist.

Amorim’s reaction on the touchline in Turin last weekend — animated, restless — hinted at a coach already pushing for higher standards. The Europa League will not allow him much time to breathe.

A long road to Frankfurt

The stakes are clear. Europa League fixtures will be officially scheduled by UEFA on Saturday, August 29, but the framework is already set. Survive the league phase, hit the top eight and march straight into the Round of 16. Fall between eighth and 24th, and a knock-out play-off awaits, with all the tension and risk that entails.

Beyond that, one date looms large: May 26, 2027. Frankfurt. The Europa League Final.

For Juventus, it is a chance to restore authority, to prove that the club’s name still carries weight beyond domestic borders. For Milan, it is an opportunity to fuse tradition with a new project and show that last season’s fifth-place finish was a staging point, not a ceiling.

Two Italian giants, one competition, and a draw that leaves no hiding place. Now we find out which of them still knows how to navigate Europe’s long, unforgiving nights.

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