Scotland suffered the ignominy an RBS 6 Nations whitewash and the wooden spoon after Italy inflicted a seventh successive defeat on Andy Robinson's side in Rome.
In what could be the final game for head coach Robinson, Scotland contributed significantly to their own downfall in an error-strewn display at the Stadio Olimpico as Nick De Luca and Jim Hamilton were sin-binned.
Mirco Bergamasco kicked a penalty, Giovanbattista Venditti crossed for a converted try in De Luca's absence and Kristopher Burton added a drop goal after 77 minutes as Italy triumphed.
Alessandro Zanni was shown a yellow card in the final quarter, but Scotland could not capitalise on their numerical advantage and their only points in an incoherent and indisciplined performance came through two Greig Laidlaw penalties.
Robinson is contracted until the 2015 World Cup but may believe he has taken Scotland as far as possible following two wins in 15 Six Nations matches - each coming on the final weekend of the championship in the past two years - and the worst sequence of results since 1998.
There were few positives the former Bath and England boss could grasp at as his side remained without a victory since the September 14 defeat of Georgia at a World Cup Scotland exited from the group stages for the first time.
Scotland and Italy have been perennial rivals to avoid the wooden spoon and if ever there was an advert for relegation from the Six Nations - with World Cup sides Georgia, Russia and Romania among those vying for inclusion - this was it.
Robinson kept faith with the players who had featured in the four previous losses and made two enforced changes following the 32-14 defeat to Ireland - the second after an injury in the warm-up for the second straight week. De Luca, a late withdrawal in Dublin, returned at centre for the concussed Lee Jones, with loosehead prop Allan Jacobsen missing out on his 65th cap after suffering an injury in the moments before kick-off.
Glasgow Warriors' Jon Welsh made his debut in place of Scotland's most-capped prop and against revered Leicester tighthead Martin Castrogiovanni, who was one of seven changes for the Azzurri and finished as man of the match.
Italy opened with purpose, spreading the ball wide, but Scotland began nervously with numerous errors and the concession of penalties.
Castrogiovanni, returning from a rib injury, set to work on Welsh early on, helping Italy establish forward momentum and Bergamasco kicked a penalty after lock Hamilton strayed offside.
The Italy wing missed a more straightforward attempt at goal after David Denton was isolated breaking off a scrum and held on to concede a penalty, which was marched 10 metres further forward by referee Alain Rolland after dissent from the Scots.
John Barclay foiled a Burton drop-goal attempt before, after 35 minutes, Scotland made forward progress.
Scotland's scrum advanced from halfway and the hosts crumbled, with Laidlaw kicking the visitors level from just inside the Italy half.
A Richie Gray knock-on at the restart immediately handed Italy possession and De Luca was sin-binned for kicking the ball out of scrum-half Edoardo Gori's hand.
Scotland, though, were handed a reprieve as Bergamasco again failed to strike his kick cleanly.
The hosts spread the ball right and left looking for an opening early in the second period and Venditti found one, bursting through a Stuart Hogg tackle to touch down with Burton converting.
Laidlaw was off-target with a Scotland penalty from the touchline after Italy turned the ball over at the restart and De Luca returned after seven points were conceded in his absence.
Tighthead Euan Murray was introduced for Geoff Cross and Gray made way for Alastair Kellock, but as soon as the former captain was introduced, Hamilton was sent to the sin-bin for an indiscretion at the line-out.
Kellock was pulled down by Zanni at a line-out, allowing Laidlaw to cut the deficit to four points with 20 minutes remaining.
As Hamilton returned, he swapped places with flanker Zanni, who was shown a yellow card for going off his feet at the ruck.
Robinson made a late change in an effort to turn the momentum in Scotland's favour, introducing Ruaridh Jackson for Laidlaw.
But fly-half Jackson could only watch as Scotland's struggles continued and Burton kicked the hosts seven points ahead with three minutes remaining.
Scotland required a converted try to salvage a draw but again lost possession to allow Italy to see out the final seconds and celebrate their first win at the Stadio Olimpico.