An Alasdair Strokosch try in the final minute of a tight battle at Loftus Versfeld in Pretoria saw Scotland edge Italy 30-29 on Saturday.
The result leaves Italy win-less on their three-game tour of South Africa having already lost to Samoa and the Springboks.
The teams swapped ends locked at 20-all after an action-packed first half that saw the sides score two tries apiece.
The second period was a very different affair as Italy buckled down, looking to strangle the result over their Six Nations rivals with fly-half Alberto Di Bernardo's boot doing the damage.
Strokosch had other ideas, crossing after the final hooter to leave Greig Laidlaw with an easy match-winning conversion.
It took less that a minute for the scoreboard to start ticking as Italy wing Leonardo Sarto ghosted over for an easy try out wide, just 50 seconds after the kick-off.
Scotland struck straight back however with Matt Scott continuing his strong tour with a try, selling the Italian defence a dummy to cruise over after six minutes.
Sean Lamont also got in on the act on the quarter-hour mark after Greig Laidlaw latched onto a fumble from Giovanbattista Venditti.
Di Bernardo and Laidlaw added the extras to all three tries before the Scottish scrum-half landed a penalty to leave Scotland 17-10 up at the end of the first quarter.
The Italian scrum made mincemeat of the Scottish pack with a series big pushes, leaving Leighton Hodges with no choice but to award a penalty try. Di Bernardo's conversion leveled the scores at 17-17 after half-an-hour.
The closing stages of the first half sparked a kicking duo between Di Bernardo and Laidlaw and the game disintegrated into an arm wrestle after the interval.
The Azzurri looked to have the result sewn up until, after laying siege to the Italian line, Scotland finally landed the killer blow as Strokosch went around Parisse, who broke the defensive line to leave of hole for the Scottish flank to slip through.
Man of the Match A mention for Strokosch, who was Scotland's top tackler, and di Bernardo, who had his best game of the June series but we'll go for Matt Scott for his excellent effort on attack, that was rewarded with a try.
Moment of the match: Obviously, Strokosch's try ruined Italy's afternoon.
Tries: Sarto, Penalty try
Cons: Di Bernardo 3
Pens: Di Bernardo 5
Tries: Scott, Lamont, Strokosch
Cons: Laidlaw 3
Pens: Laidlaw 3
Italy: 15 Andrea Masi, 14 Leonardo Sarto, 13 Luca Morisi, 12 Alberto Sgarbi, 11 Giovanbattista Venditti, 10 Alberto Di Bernardo, 9 Tobias Botes, 8 Sergio Parisse (capt), 7 Robert Barbieri, 6 Joshua Furno, 5 Marco Bortolami, 4 Leandro Cedaro, 3 Martin Castrogiovanni, 2 Davide Giazzon, 1 Matias Aguero.
Replacements: 16 Leonardo Ghiraldini, 17 Alberto De Marchi, 18 Lorenzo Cittadini, 19 Antonio Pavanello, 20 Alessandro Zanni, 21 Alberto Chillon, 22 Gonzalo Canale, 23 Luke McLean.
Scotland: 15 Peter Murchie, 14 Tommy Seymour, 13 Alex Dunbar, 12 Matt Scott, 11 Sean Lamont, 10 Tom Heathcote, 9 Greig Laidlaw (c), 8 Johnnie Beattie, 7 Alasdair Strokosch, 6 David Denton, 5 Al Kellock, 4 Tim Swinson, 3 Euan Murray, 2 Scott Lawson, 1 Alasdair Dickinson.
Replacements: 16 Fraser Brown, 17 Jon Welsh, 18 Moray Low, 19 Grant Gilchrist, 20 Rob Harley, 21 Henry Pyrgos, 22 Duncan Taylor, 23 Tim Visser.
Venue: Loftus Versfeld, Pretoria
Referee: Leighton Hodges (Wales)
Assistant referees: Lourens van der Merwe (South Africa), Cobus Wessels (South Africa)
Television match official: Deon van Blommestein (South Africa)