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If I bought 100 shares of a stock in May at $100, another 100 at $90 in June, and then sold everything today at $85 what would be my capital loss for tax purposes in April 2010? Would I calculate an average price of $95 as my buying price?
 

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Yes, you use average cost base as the basis for calculating your gain/loss.

Since you sold all your shares your cost is going to be $19,000 and your proceeds on disposition will be $17,000 for a loss of $2,000 - net taxable loss of $1000 (ignoring trading costs).
 

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And if you only sold half your position the '$pershare' ACB would be that same average cost - (100sh * (90+100/2) = $9500.
 
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