Too many times.
3 crashes. Rescued by helicopter, ambulance and by a passing motorist.
Twice called the OH out. Once suffering from extreme cold, snowing and already had a couple of punctures.
Another time, discovered my frame had broken. Could have ridden home, but once I realised, too worried.
Leaving the office, my cassette went. Colleague gave me a lift home. On another similar occasion, used a toe strap to turn the cassette into a fixed gear and was able to ride the last 10miles home.
Puncture 3 miles from home. Complete darkness. Rang my daughter and she brought out a spare wheel (benefit of having a spare set of wheels ready to go) and I was able to finish my journey.
A long time age, when I was 14, me and a school mate attempted to do Prescot, Llangollen and back. About 90 miles. We were within 15 miles of home and my mate was too exhausted and he called out his dad.
Similarly, the first time I rode the London Brighton. I'd ridden to the start and got as far as Tunbridge Wells on the way back beforehitting the "wall". Would have been 140 miles there and back. The next 3 years rode and managed to get all the way back.
The above spans about 60 years of cycling, so perhaps not that bad.