It seems that all raids I have heard of were heavily punished but with at least half surviving. I cannot find any raid where all bombers were wiped out.
If you mean a "heavy bomber flight" being one that was completely destroyed, then yes... And it happens to be a very famous one...
The Doolittle Raid consisted of 16 bombers that bombed Tokyo on April 18, 1942. All but 1 of the original 16 aircraft crashed in China, with one landing in Russia.