To me it looks like he is so much in the habit of taking a nap at 9.30 that his body clock is making him nod off, it might be hard but push past it as quickly as you can because that first nap looks UT needing a resettle.
I wouldn't read much into the last nap, he will have been UT due to having a car nap and sometime we just can't avoid car naps, that's life.
Maybe try some pain meds for the teething before nap time.
Yes I had assumed UT from car nap and was going to put him down later but then I wasn't sure whether to do that as it would shift everything much later and change meal times etc. Anyway, what's done is done! We are definitely on top of pain meds (calpol is my new best friend!) so will continue to push the nap back as best I can.
