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.
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$\begingroup$ I could be mistaken, but strategic bombers usually fly solo (such as the B-2). Did you mean heavy bombers, such as those used during WW2? I ask for clarification because you say half were wiped out, which hints at big formations. $\endgroup$– user14897Commented Sep 5, 2019 at 21:40
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2$\begingroup$ In WWII strategic bombers flew missions to support the national strategy - B-17s and Lancasters bombing cities. Bombers not flying strategic missions were supporting specific military tactical objectives, interdiction etc., and are therefor called tactical bombers - B-25s attacking rail yards. Or B-17s bombing troop concentrations in Normandy; a strategic bomber being used for a tactical mission. $\endgroup$– John KCommented Sep 6, 2019 at 0:42
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1$\begingroup$ Ploesti's the worst one I can think of. About a third of the bomber force shot down. $\endgroup$– John KCommented Sep 6, 2019 at 1:02
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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.
Source: Wikimedia
answered Sep 5, 2019 at 23:03
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3$\begingroup$ Not sure this counts. Wiped out to me means "shot down". $\endgroup$– John KCommented Sep 6, 2019 at 0:37
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2$\begingroup$ @JohnK A plane that crashes due to weather, malfunction, or other actions not due to hostile forces is still just as lost as one shot down. I think maybe "didn't return safely" is a better definition. $\endgroup$ Commented Sep 6, 2019 at 1:06
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9$\begingroup$ This raid was a one-way mission from the inception. $\endgroup$– Dohn JoeCommented Sep 6, 2019 at 8:03
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3$\begingroup$ @DohnJoe: Weren't they originally planned to land in airfields in southern China, get refuelled and rearmed there, and then fly back the other way (with them only being all forced to bail out over occupied China due to them having to launch the raid too early [due to a suspected Japanese submarine sighting], when they were still out of range of the destination airfields)? $\endgroup$– VikkiCommented Oct 7, 2019 at 1:55
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$\begingroup$ The wikipedia page you linked says the Doolittle Raid was for morale purposes, and not for strategic purposes. So it isn't a strategic bomber raid. $\endgroup$ Commented Sep 19, 2021 at 23:53