Two situations, both caused by inattention, one mountain biking, one on the road. And then a multi-puncture record.
While mountain biking on a local suburban loop, I was on a section of boring dirt "sidewalk" and zoning out, when I suddenly realized someone had piled up a bunch of cactus pads across the trail. Too late to do anything, even bunny hop, I plowed right through it. Sure enough, both tires/tubes went instantly flat. I found each tire filled with spines. The worst was that these were brand new tires, now completely destroyed - even with all the spines pulled out, there remain "mini-spines" - backward facing stiff hairs that force the cactus spines deeper into your flesh, which in a tire can be a cause of repeated flats.
I called my wife to come pick me up.
Near the end of a long road ride, I was only a mile or so from home and weary. Zoning out again, I let my front wheel wander into a long crack in the asphalt. The crack was just tire width, and jagged. Again, both tires/tubes taken out. Again I called my long-suffering wife!
The worst ride for punctures was a ride with my friend, Jim, who early in the ride suffered a double snake bite on his front tube - two double punctures on each side of the tube from slamming into a small pothole. Total of four holes two patch. It took him two re-inflations to discover all of them!
Later in the ride, we had temporarily ended up on the tail of a large club ride. Somewhere near the front, someone managed to flip the steel cover off of an 8 inch pipe coming up to the surface of the road. The cover got knocked around as riders swerved wildly to avoid it. Jim never got to the hockey scrim with the cover, as he slammed into the open pipe end, and once again got double snake bites on his front tube!
That made for a total of eight holes in his tube on a single ride! Anybody got more than that???