Just a small point. In one of your posts above you said QB which usually means QuickBooks not Quicken. We are talking about Quicken right? And I didn’t see you mention what version you are using.
I didn’t understand your problem either. But Just in case you are doing it the wrong way,The proper way is to set up a credit card ACCOUNT and enter the charges into it when the purchase is made and assigning it to a category. Then when you pay the bill you TRANSFER the payment from your checking account to the credit card account. Then when you download the payment from the bank you match it to the one you already entered.When you enter the payment in your checking account you put the credit card account name in for the category using square brackets around the name to indicate it is a transfer...like this... [credit card] or newer versions have a Transfer column.I used to do it the wrong way for years! Then I wised up and now enter them properly. I would split my credit card payment into all the categories on one transaction in my checking account. And since I always pay more than the bill I would need to figure the difference and put it to another category. But then I needed to have them entered on the date the charges actually happened. So I finally set up a credit card account. It makes it much easier to enter and balance!