The latter approach reports each ticket sale, be it for gain or loss. It is a frustrating process but it reports no issues in the software.
The amount reported on the IRS form 1099-K box 1a needs to equal the Proceeds reported for the multiple entries of IRS form 1099-B.
In your case, all the dates are within the year, so there are no long-term vs short-term issues. I would report the date that I paid for the season ticket package as the purchase date. And the dates of individual games as the date of sale.
For next year, if you maintain a spreadsheet of the various ticket sales, you may be able to group the sales into two entries, sales for gain and sales for loss. You would have the spreadsheet information as evidence and backup should a tax authority have a question at a later time.
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