Liam Henderson plays pivotal role in Coppa Italia upset as Scottish midfielder's contract puts clubs on alert

Henderson provided two assists and scored in a penalty shootout as Empoli overcame Tuscan rivals Fiorentina at the Stadio Artemio Franchi.

After a 2-2 draw, it was Empoli who prevailed 4-3 on spot kicks to provide one of the shocks of the round given Fiorentina are flying high in Serie A this season.

Empoli have acquitted themselves strongly as well during the 2024/25 campaign. Roberto D’Aversa’s side currently sit tenth in the Italian top flight and now have a last-eight tie away at Juventus or Cagliari to look forward to following their success in Florence.

Many of the Scottish headlines this season have been made by Scott McTominay and Billy Gilmour at in-form Napoli, but Henderson - who has played in Italy since 2018 - continues to perform well at Empoli.

Henderson put in one of his best displays of the campaign against Fiorentina on Wednesday night, posting his first goal involvements of the season.

On four minutes, he pressed high to dispossessed the hosts to send Emmanuel Ekong through on goal just four minutes in and he made no mistake in finishing past Fiorentina goalkeeper Pietro Terracciano.

Moise Kean levelled for Fiorentina on 59 minutes and were then expected to go on and win when Riccardo Sottil put them ahead on 70 minutes. However, Henderson inspired Empoli to equalise five minutes later with a gorgeous through ball to send Sebastiano Esposito in and he finished to force extra time. The match ended up going to penalties, with Henderson scoring Empoli’s third kick as they won 4-3 in the shootout.

It was an emotional night in Florence, with Fiorentina playing their first match since their young midfielder Edoardo Bove collapsed during Sunday’s Serie A match against Internazionale. Bove watched on from hospital bed as supporters all across the stadium held up No 4 banners in support of the 22-year-old Roma loanee, who remains in a stable condition.

Henderson has been at Empoli for three years but spent last season on loan at Palermo in Serie B. He has become a regular in the squad since D’Aversa took over in the summer, although his deal at the Stadio Carlo Castellani is set to expire at the end of the season. His contract situation will be monitored by a number of clubs, with the 28-year-old able to speak to potential suitors next month.

A product of the Celtic youth academy, Henderson famously provided two assists to help Hibs win the Scottish Cup while on loan in 2016. He left Scotland for Italy in 2018 and has played for Bari, Hellas Verona, Lecce, Palermo and Empoli in both Serie A and Serie B during his six years abroad.

Capped at under-21 level, Henderson has yet to be called into the full Scotland squad, and is one of six Scots currently playing in Italy along with McTominay and Gilmour (Napoli), Che Adams (Torino), Lewis Ferguson (Bologna) and Josh Doig (Sassuolo).