Since losing a World Cup semi-final against Germany in Turin in 1990, England have been eliminated on penalties in five more tournaments, including Sunday's exit at the hands of the Italians.
Italy won the shootout 4-2 at the Olympic Stadium in Kiev following a 0-0 draw after extra time, setting up a clash with Germany in Thursday's semi-final in Warsaw.
For England and Italy, a shootout was a nightmare scenario they wished to avoid as both nations have dreadful records overall with the Azzurri's 2006 World Cup final triumph against France a rare bright spot.
On the night, it was clear that Italy were striving to end the contest in normal time by creating a stream of chances, but they were unable to beat England's solid defence in which goalkeeper Joe Hart and central defender John Terry were outstanding.
In the end, it came down to penalties again and this time, with Andrea Pirlo dinking one in with icy aplomb, Italy took full advantage of England's shredded nerves as Ashley Young slammed his shot against the bar.
That turned the pressure up for Ashley Cole, scorer of a fine penalty shootout goal for Chelsea in last month's European Cup final triumph over Bayern Munich, but this time he placed a weak effort within reach of Gianluigi Buffon.
Captain Steven Gerrard and striker Wayne Rooney had both scored to give England a 2-1 spot-kick advantage after Riccardo Montolivo had shot narrowly wide, but the Italians suddenly turned from jittery kittens into masters of their destiny.
Alas for Young and Cole, their failures will go down in the miserable annals of England's penalty pain, joining such wretched memories as Chris Waddle's kick sailing over the bar in Turin and Gareth Southgate's scuffed effort, easily saved by Andreas Kopke, that sealed another German semi-final triumph at Euro 96.
HOME SOIL
England, in that tournament on home soil, had at least managed to beat Spain on spot-kicks in the last eight to claim their place in the semis.
Italy also suffered penalty miseries of their own in the same period, but it was nothing compared to England's succession of heartbreaks which continued in 1998 when Paul Ince and David Batty failed from the spot as Argentina prevailed in the World Cup second round following a 2-2 draw.
The English nightmares returned at Euro 2004 with a shootout defeat by hosts Portugal in the quarter-finals when David Beckham skied his kick way up into the Estadio da Luz and blamed a dodgy penalty spot.
Portugal were again England's nemesis two years later at the World Cup with another quarter-final defeat on penalties as Wayne Rooney was sent off and Jamie Carragher missed his twice-taken kick in a 3-1 shootout loss following a 0-0 draw.
Those 2006 finals in Germany were, of course, a crowning glory for Italy with Fabio Grosso confidently striking in a winning penalty when Marcello Lippi's men scored all five spot- kicks to edge out France after a 1-1 draw.
That triumph may have given Italy a decisive psychological advantag
