Yes, you can group your T5008s together. It would be a good idea to create a spreadsheet with all the information from all your separate T5008s, so if the Canada Revenue Agency (CRA) asks, you can give them the spreadsheet.
For Box 14 you can enter December 31 if you are submitting multiple transactions.
Please remember to convert the USD amounts to CAD. You can get the exchange rate from this Bank Of Canada webpage: Exchange Rates
Please see this TurboTax Article for more information on the T5008 Slip: T5008 Slip – Statement of Securities Transactions
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