A broker or barter exchange must file Form 1099-B, Proceeds From Broker and Barter Exchange Transactions, for each person:
You will need to enter the Property Description, Date Acquired, Purchase Price (or Basis), Date Sold, Sales Proceeds, etc. Note: The Form 1099-B that you received may or may not report the Date Acquired or the Cost Basis. This information is generally maintained by you and is needed to complete the proper reporting of the transactions.
If you sold stocks, funds, or similar property that was acquired through several different purchases, you may report the sale on one line and enter "VARIOUS" as the date acquired. If the sale included both short-term and long-term gains or losses, you would need to enter the sale on separate Forms 1099-B.
Also, be sure to make the appropriate selection on the screen titled Investment Sales - Category.
You may wish to refer to IRS Publication 550 Investment Income and Expenses for additional information.