The Azzurri are facing the prospect of missing out on the summer showpiece for the first time since 1958, while Sweden could suffer the ignominy of failing to qualify for their third consecutive finals.
Here, Press Association Sport looks at five talking points ahead of the first leg of this play-off.
Can Italy avenge the 'biscotto'?
At Euro 2004 Italy faced an anxious wait to see if group rivals Denmark and Sweden would avoid securing the one scoreline that would eliminate the Azzurri from the competition. The Scandinavian countries were angered by suggestions they would throw the game to progress together but, lo and behold, the match did finish 2-2 in Porto. This affair became known as 'il biscotto' - or the biscuit - in Italy, a slang term for an underhand arrangement in football and elsewhere in life. Sweden and the Danes have always denied indulging in such immoral tactics, but Italian fans remain embittered.
No Zlatan, no cry?
One crumb of comfort for an Italy squad who have underperformed in qualifying is the absence of Manchester United striker Zlatan Ibrahimovic, who retired from international duty in June 2016. Sweden are still confident in front of goal, with Marcus Berg hitting four in an 8-0 demolition of Luxembourg, but Friday's visitors will undoubtedly be grateful that Ibrahimovic is not on the prowl in Stockholm. Daniele De Rossi said: "Even at 40 with a broken leg I'd never want Ibra against me."
While Italy have always been best-known for their resolute defending, many lethal strikers have worn the famous blue shirt: Roberto Baggio, Francesco Totti and Alessandro Del Piero to name a few. But despite a resurgence of the prolific 'bomber' in Serie A - Ciro Immobile is already on 14 goals for Lazio this season - the Azzurri have struggled to notch on the world stage lately. Since thrashing minnows Liechtenstein 5-0 in June they have scored only three goals in four matches and in Sweden they will not have a fully-fit frontline as Immobile and Torino's Andrea Belotti are still nursing knocks.
No Swede dreams for Italy
Their scoring worries aside, Italy cannot hope to simply park the bus in the Swedish capital and wish for better days in the San Siro return fixture. Sweden were unlucky not to beat France to first in Group A and such was the strength of Janne Andersson's team in qualifying they managed to pip Holland to the play-off position. Sweden are also unbeaten in their last seven matches on home turf and boast a selection featuring many household names from the English leagues and European top flights.
Focus on Forsberg
One of the Scandinavian stars who is steadily growing his reputation on the continent is RB Leipzig winger Emil Forsberg, who could be key against Italy. The 26-year-old learned his craft in the Swedish Allsvenska before helping Leipzig gatecrash the Bundesliga, where in May they secured a shock second-placed finish. In Gazzetta, former Sweden international Tomas Brolin said of his countryman: "He has personality, he can accelerate to beat his man and help the team in that way."