I am filing for my stock transactions. Do you need to file a separate 1099-B for every single stock transaction? So if you have 20-30 transactions you need to submit 20-30 1099-B? What is confusing is that in box 2 it wants gross proceeds for the year and than in boxes 1a it wants the date of sale which would only be applicable to one specific transaction. How can you put a date in box 1-a if all the gross transactions reported in box 2 were all on different dates?

You do not file any 1099-B forms with your 1040. Just make sure that the proceeds you report on Schedule D add up to the amounts reported on the 1099-B's you have received. You should have received 1099-B forms along with any 1099-DIV and 1099-INT forms from your broker.