If the clutch oil was real dirty before it could have damaged the synchro in 2nd. That is usuallt the one that goes first. My soft top has no synchro in 2nd. I just skip second most of the time and go straight to 3rd.

Clutch oil

What vehicle are we discussing here?
Dirty oil, in and of itself (or for that matter in the clutch or elsewhere), will not damage the transmission synchros, although worn synchros can result in the oil becoming contaminated - as a side note - a clutch, contaminated with oil, will sometimes burn the oil off (heat generated when it slips), leaving a sticky residue that causes the clutch to drag, and that drag can cause grinding and increased wear on the synchros.
It is possible that the grinding is caused by not disengaging completely, it is also possible that it is caused by worn synchros, but, to the best of my knowledge, double clutching
done correctly can eliminate the grinding that results from worn synchros, 100% of the time - that it does not always work for you could point to two things - one, the synchros are not the problem, the clutch is, or, two, you need more practice, you're not getting it right.