Only thing I can say is, it might.
Socket 1156 was noted for supporting 4x4GB in its hey day. Some manufacturers supported 8GB dimms up to 32GB of memory even though there was noting in writing stating support. With 2 revisions of your board, multiple BIOS versions, CPU combinations and different 8GB modules available, all of these are going to pay a role in your success.
Since you have already purchased the memory and run into a boot issue, I would try setting the voltage and memory parameters manually. Your CPU in conjunction with the memory you have chosen may or may not work together. Can't be more definitive given the lack of information we have about your hardware. P55 was released in Q3, '09. This is a gamble.