How do I match two transactions from different dates to one expense? The expense is not showing up in match transactions.

Hello jaywigston,

It's awesome to see you're putting the extra effort into making sure everything gets added from your bank feed correctly. It's a great habit, which helps unlock the full power of this integration to make your bookkeeping easy. It's the best way to simplify reconciliations, while also produce insightful reports. I'll be happy to help you sort this out. 

The best way to match two transactions to a single expense in your books is by using a bill, or recording them separately. When you record an expense, you're indicating to QuickBooks pay a specific amount left your bank or credit card account. Using a bill gives you additional control, as these are designed to allow multiple payments. You can create a bill by clicking + New and selecting Bill. You'll be able to select this bill to match a smaller amount from your bank feed. Check out this great article for more info on recording bills: Enter and pay bills

I've got your back. Let me know if there's anything else I can do to help!