Last November I was doing a century race with a couple of friends. At mile 18 I hit a pothole and damaged both rims so bad that the tubeless tires wouldn't hold air. I sent my buddies on to finish the race. One of the bike patrol guys had pliers and extra tubes, so 45 minutes later I was rolling again and hoping the wheels would hold for the next several hours.
By that point, nobody riding in the area wanted to go my pace, so I was on my own. At mile 40, I finally caught up to riders that could at least stay in my draft, and I pulled anybody along who would come.
I finally caught one of my buddies at the mile 75 rest stop (he'll never live that down), and we finished the race together in just under 6 hours. I laid down in the ground for 20 minutes feeling like I was going to heave up everything that I'd ever eaten. That was much slower than any other century race I've done, but the one I'm most proud of simply because I finished in the face of the most adversity.