Here, BBC Sport highlights the key battles likely to be played out at Hampden.
JAMES McFADDEN v FABIO CANNAVARO
Striker James McFadden is the darling of the Tartan Army, having pitched in with four goals in what has been a thrilling qualifying journey for Scotland.
The pick of the bunch was his long-range strike that stunned France in Paris.
And that goal sums up the 24-year-old, who struggles to hold down a starting place at Everton.
When he pulls on the blue of Scotland, McFadden is a whirlwind of energy and invention and certainly no respecter of big-name reputations.
He may have to play up front on his own but he is the home player most likely to turn the game with a moment of magic.
While he is not the tallest of central defenders, their are fewer with a bigger standing on the world stage than Fabio Cannavaro.
The Italy skipper was voted World player of the year and European footballer of the year in 2006.
Not blessed with great pace and lacking height, the Real Madrid star is an expert reader of the game and has the knack for being in the right place at the right time.
Having lifted the World Cup on what was his 100th appearance for Italy, Cannavaro has done it all for club and country.
BARRY FERGUSON v GENNARO GATTUSO
This promises to be an intriguing match-up between two old team-mates.
Ferguson was impressive in the last home win over Ukraine, dictating the pace of Scotland's play with a simple passing game and digging in with some important tackles.
With a white-hot atmosphere expected at Hampden for the winner-takes-all clash, Ferguson's calm head is sure to come in handy.
The captain is also the organiser-in-chief in the middle of the park and it will be important for him to get on the ball, with Italy always comfortable in possession.
Gattuso, Ferguson's former team-mate at Rangers, is the kind of player everyone wants in their own team but hates as an opponent.
A bustling, snarling midfield enforcer, 'Rino' never gives an inch in the midfield battle, but there is far more to him than ball-winning.
Twice a Champions League winner with AC Milan, Gattuso has curbed his once short fuse without losing any of his competitive edge.
DAVID WEIR v ANTONIO DI NATALE
Walter Smith produced a masterstroke when he persuaded David Weir to end his international exile.
The Rangers veteran may not be the quickest defender, but his experience and composure has contributed hugely to Scotland's mean goals against record.
Partnered by the brave and athletic Stephen McManus, Weir is the man who marshals the troops at the back and he is sure to be kept busy at the weekend.
Italy's forward line has changed from game to game since Roberto Donadoni took over the managerial reins last year, but Antonio Di Natale can count himself unlucky if he is not included at Hampden.
The Udinese striker scored twice in the recent win in Ukraine and appears to have at long last shaken off the tag of wayward genius and found a high level of consistency.
The diminutive attacker is likely to be supporting central striker Luca Toni in a 4-3-3 formation and, with his pace and close control, will be a real danger cutting in from either flank.
The quality of Italy's forward options is underlined when we see players of the calibre of Alessandro del Piero and Filippo Inzaghi left out of their travelling party.
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