Reigning European champions face a real scrap just to qualify and be able to go and defend their title in Germany next summer, but the spectre of facing bogey side North Macedonia will bring back some bitter memories.
North Macedonia famously scored a stoppage time winner to beat Italy and stop them from qualifying for last year's World Cup - while they also drew with the Azzurri in the home fixture of this group.
Italy will be sick of the sight of them, but above revenge the main aim at Rome's Stadio Olimpico is to win three points that will put them level with Ukraine, who currently occupy the second automatic spot behind England.
That will set-up a huge clash between the pair in Germany next week - but first they need to see off the ghosts of qualifying groups past.
And considering the recent history between the two teams, what's at stake for Italy here and by the 29 fouls, with five players giving away multiple free-kicks, then fouls looks like the way ahead for us...
Gianluca Scamacca certainly likes to put himself about a bit - he scored at Wembley in Italay's 3-1 defeat but the former West Ham striker is of more interest to us in the fouls market than the goalscorer betting.
He's 5/61.84 to score, which he's managed just once in his 12 games for Italy, and 4/51.80 to have 2+ fouls in the game - which he's managed four times.
Scamacca even managed to give two fouls away just from a 25-minute substitute appearance against Malta - and with the pressure well and truly on here for Italy he'll be flying around the pitch in Rome.
Stefan Ashkovski has played at right back and in midfield for North Macedonia during qualifying - starting four games and giving away a foul in three of those.
He's given away multiple fouls in just one game so far in qualifying, but, yep, you guessed it, that was in the reverse fixture where he gave away three fouls against Italy in Skopje.
Now with Italy thirsty for revenge and a rampant crowd in Rome, Ashkovski has all the conditions there for another multiple foul outing.
And he's 5/23.50 for 2+ fouls against Italy - so we'll take that.
One of Italy's Euros heroes, Federico Chiesa has missed the last two international windows through injury, but Lucianp Spalletti can finally call upon him for the first time since taking the Azzurri job.
He's not played for Italy since the Nation League finals in June - so he'll be raring to go and has already spoken about what a huge game this is.
Chiesa is 8/131.61 for 1+ foul here and despite him giving away just three fouls domestically this season, I still like him to deliver here.
It's more circumstantial evidence than any cold hard facts of the season so far, but in three of his last four competitive games for the Azzurri he's had multiple fouls and he finished off last season with a foul in 16 of his last 20 matches.
When he's fit and firing he's flying around the pitch, and if handed the start on Friday then I'll also be eyeing up a side bet on the 3/14.00 for him to have 2+ fouls. But we'll keep it to one for our Bet Builder in Rome.