I sold some shares of ESPP stock this year at 2 different times. I think I understand how to figure out the cost basis, but do I have to file two schedule D's with my 2010 taxes since the shares were sold at different times (June 2010 and October 2010). Help!

“ but do I have to file two schedule D's with my 2010 taxes since the shares were sold at different times (June 2010 and October 2010)”-----> No; you need to file only one Sch D for all of the 2010 transactions. You must keep accurate records that show the basis of your capital asset.