Cashed in mutual fund June 2008 received 1099b purchased mutual fund sept 1992 net gain 14200 dollars after cashed in. filed and paid taxes on 1099div yearly from 1992 to 2008. Will I pay taxes on 1099b amount

The 1099B lists the proceeds that you received in the sale. You do not owe taxes on that entire amount, just on any capital gains that the sale made for you. You report caital gains from sales of mutual funds on Schedule D. You have capital gains if your proceeds from the sale exceeded your cost basis, or a capital loss if the proceeds are less than your cost basis. The tricky part is in figuring out your cost basis. I take it that you have been reinvesting dividends and capital gain distributions all along - hence you have been buying shares at prices that varied as you bought the shares through reinvestment. Your cost basis in the entire account is equal to your original investment amount plus the total of all amounts reinvested by you from inception of the account through to the date of sale (I am assuming here that you sold all shares in 2009, and in previous years had never sold off any shares - please correct me if I'm wrong on that). Your account statement from the mutual fund company that reports the sale may actually show what your total cost basis is - most have been keeping that data since at least the early 90's, so check your year-end statement carfeully. If the cost basis isn't listed on your statement, then you can either (a) call customer service and ask if they have the data, or if that doesn't work (b) go back through your financial records and add up all the reinvestments you've made over the past 18 years. If you have kept year-end statements you'll find the info there. Or if you have your old tax records you can see how much you reinvested - include both your reinvested dividends and capital gain distributions.