Ladbrokes spokesman, Nick Weinberg, said: "Losing penalty shoot outs isn't just an English disease. The Italians have had more than their fair share of spot kick heartbreak.
"It's got to the point where you have to wonder whether it's too big a psychological hurdle to overcome."
Former darling of AC Milan Andriy Shevchenko is 2/1 to score at any time.
Weinberg added: "Shevchenko will want to remind the Italians exactly what they'll be missing next season. He could break Italian hearts by delivering one final knock out blow to his adopted country."
LATEST BETTING
90 minutes
Italy 4/7
Draw 11/5
Ukraine 5/1
To qualify
Italy 1/5
Ukraine 16/5
To win via a penalty shoot out
Italy 10/1
Ukraine 12/1
To score a penalty (extra time and penalty shoot out does not count)
Italy 9/2
Ukraine 6/1
To miss a penalty (extra time and penalty shoot out does not count)
Italy 16/1
Ukraine 20/1
What will Happen First to Luca Toni ? ( player must start - 90mins only )
Play Full 90 mins 5/2
Score 11/4
Subbed 7/4
Booked or Sent Off 5/1
Set Up a Goal 7/1
What will Happen First to Alberto Gilardino ? ( player must start - 90mins only )
Play Full 90 mins 5/2
Score 11/4
Subbed 7/4
Booked or Sent Off 5/1
Set Up a Goal 7/1
What will Happen First to Andrei Shevchenko ? ( player must start - 90mins only )
Play Full 90 mins 8/11
Score 7/2
Subbed 6/1
Booked or Sent Off 7/1
Set Up a Goal 8/1
Miss a penalty 33/1
Most Cards
Ukraine 8/13
Italy 9/4
Tie 4/1
Number of Italian players to score in the match ? ( 90mins only )
None 3/1
One 6/4
Two 5/2
Three or more 10/3
After Eighty ( Goals After 80mins extra time doesn’t count )
None 8/15
One 9/4
Two 13/2
Three or more 14/1