Investors & landlords

I'm still unclear,  I sold a fund which had some 60 separate purchase dates for the uncovered portion.  Should I provide the total cost or should I separately enter each purchase date, number of  shares purchased  on  that date and the cost and proceeds for the purchase and sale of these shares? If the answer is a one entry total cost, should I just retain the backup or submit it separately to the IRS?  Is Quicken history of each purchase and its cost considered adequate backup?