Yes, I had a funny moment with an assessor when I had my car stolen off the driveway, my only car insurance claim in nearly 30 years.
He was sat down going through the paperwork, asking questions about the car's condition and service history, etc., presumably to arrive at a valuation. Then he threw in, "has there been any previous claims on the vehicle?"... thinking he meant accident damage or theft etc., I answered no, not as far as I knew - but he immediately responded by telling me I had had a windscreen on such a date, the value of the claim, etc.. It was a few years previously, and to be honest, I had forgotten about it. They hadn't though.
There was a pregnant pause as we looked at each other for a moment, then I apologised for failing to remember and we carried on as if nothing had happened.
It was very odd, happily the claim was paid out quickly and without any further fuss.