Stefano Pioli’s future at AC Milan is uncertain as the seven-time European champions prepare for Thursday’s first leg of their Europa League quarter-final with Roma.

Never in the fight for the Serie A title and dumped out of the Champions League at the group stage, the last-eight Italian derby will be the biggest two matches of Milan’s season so far.

They will also be crucial to Pioli’s chances of staying in the Milan dugout as the 58-year-old has been more under fire this term than at any other point since the troubled early months of his tenure back in 2019.

Pioli was expected to be replaced by Ralf Rangnick in the summer of 2020, but a sudden burst of hot form when that season restarted in the midst of the coronavirus pandemic and very public outrage from directors Zvonimir Boban and Paolo Maldini about how the talks with Rangnick were handled kept him in place.

Keeping him turned out to be a winning move as Pioli brought Milan the Serie A crown two years later, but Pioli is now out of favour with fans for not keeping up with Napoli last season nor with Inter this term.

A run of five straight Milan derby defeats has not helped neither has the prospect of officially conceding this year’s Scudetto to Inter in the next clash with their local rivals later this month.

Also exacerbating the situation is the feeling that Milan have been overtaken by Inter on the continent since Pioli dragged them back to the top table after years in the doldrums.

But a deep run in the Europa League, a competition Milan have never won neither in its current guise nor as the old UEFA Cup, would give Milan extra reason to be happy with the final weeks of a largely disappointing season.

Seven straight wins in all competitions have taken Milan to the last eight and to a likely second-placed finish in Serie A, helped by a remarkable drop off in Juventus’ form.

“We’ve never stopped believing in what we do, we’ve never stopped believing in the players and they haven’t stopped believing in us,” said Pioli after Saturday’s 3-0 win over Lecce.

“When a team struggles so long but doesn’t give up, it recognises when it’s got through the rough patch.”

De Rossi on a high

Pioli will have Ruben Loftus-Cheek back after the England international was suspended for the weekend’s stroll past lowly Lecce.

Loftus-Cheek has been in the form of his life in 2024, netting nine times since the turn of the year from his advanced midfield position.

Four of those goals came in previous Europa League knockout ties with Rennes and Slavia Prague which were comfortably won by Milan.

The major decision Pioli faces is who to play alongside Matteo Gabbia in central defence with Fikayo Tomori suspended, with Simon Kjaer favourite over Malick Thiaw who is returning from injury.

Milan have already comfortably beaten Roma twice this season but that was while Jose Mourinho was still in charge, and the capital club promised to be a wholly different proposition this time around.

Pioli’s Roma counterpart Daniele De Rossi is coming into Thursday’s match at the San Siro on a high after winning the Rome derby at the weekend and keeping his team in the Champions League hunt.

The trip north will show just how much has really changed for Roma under De Rossi as it was their most recent defeat away to Milan in January that did for Mourinho.

Since then Roma have only lost two of 15 matches, one to champions-elect Inter and the other to Brighton in the previous round of the Europa League after killing their last-16 tie against the English team in the first leg.

De Rossi’s future is also in doubt as he was only hired until the end of the season but such is the positivity surrounding Roma with their former captain in charge that a decent showing in this tie could get him the job on a permanent basis.