Once, 20 years ago. Almost sank Dad's Bass Boat. Had no bilge pump either. We just opened the throttle and both of us went to the front of the boat to get it on plane, then cruised around till it all ran out, went for a swim and put the plug in. Had a normal day skiing after that.
On the other hand, I haven't used transom straps for years now but after all the pics lately of people losing boats I will have them from now on so I will probably forget to take them off this summer.