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In 1999 I purchased a stock on two separate occasions at different prices. By the end of 1999 - I sold a small portion of the stock on five occasions for a loss.

You must use FIFO (first in first out) on your basis (which is what you paid plus commissions) so the first stock you bought would be the first you sold. Each of your 2 purchases would have a basis of Y total paid divided by X shares. This gives you your per share basis. If you need further information, let me know.
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