This is the most frustrating and time consuming bug/issue I have experienced with many versions of Quickbooks over the last 7-8 years and it is truly amazing that it has not been addressed. This issue has occurred to me with a couple versions of QB desktop and Enterprise 22. 

My client has a bank account that only receives customer payments.  With the exception of the weekly transfer I make out of the account,  EVERY transaction brought in is new to QB.  When I import the new transactions in,  QB looks tries to match them with every unreconciled transaction in the register that has the same amount. It fails to filter out a possible matches that have a different date. I import transactions weekly and by the last week of the month,  Half the transactions I've imported are auto-matched incorrectly.  As others have noted, it can take several attempts with the "Not A Match" drop down selection to get the auto match to clear.  It often is quicker for me to pull up the register and manually type them in.  

If Intuit is unable to come up with the programming to fix or mitigate the issue, I would like to see another drop down list item in the action column. "Enter as New Transaction". It would simply ignore trying to auto match, apply any applicable rules and enter the transaction to the account.