Yes, report the two transactions separately. While your 1099-B combined both sell transactions, the financial reality appears to be that these transactions--the ISO and the ESPP--began as two distinct transactions and thus, you should treat them as two transactions.
Because you have purchases and sales involving the same security, be mindful of the wash sale rule. The wash sale period is 30 days before, and 30 days after the sale of the security in question. That is, if you sell a security at a loss, and then you buy the same, or similar security, within that 61-day window, you will trigger the wash sale rule. The wash sale applies across all of your accounts wherever they are held.
@bluecloud33
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