The current world record for the longest penalty shoot-out in a first class match is 48 penalties during the 2008 Greek Cup Final when Olympiakos Pireus beat AEK Athens 23-22. However, the record for the highest score in a penalty shoot out was set in the 1988 Argentine Championship, when Argeninos Juniors beat Racing Club 20-19 after 44 penalties.
Nearly had a heart attack watching those pens...
that had to be some sort of record for most penalties ever taken in a single match