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Currently you can clear browsing data from now up to one day/week/month etc.

Is there a way to do the opposite and clear everything older than one day/week/month?

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    Take a look at eHistory extension. You can clear history using a custom date range. – w32sh Jul 20 '16 at 6:38
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Unfortunately, it seems that the Chrome developers only catered to adolescents needing to hide browsing history from their parents. Us older people need therefore to use third-party software, or use a database browser to attack directly the history database.

Here are a couple of add-ons that might help. They are not recent, and I do not know if they still work :

In the Do It Yourself way, see the thread How can I delete all web history that matches a specific query in Google Chrome, where two solutions are proposed :

  1. Hacking the Chrome history page itself, chrome://history-frame/, by JavaScript injection, although the described solution deletes all history, so still needs to be improved to work in a selective manner.

  2. Using an SQL viewer to manipulate directly the Chrome History database, normally found under Windows as the file %localappdata%\Google\Chrome\User Data\Default\History, as is detailed in this answer. I suspect that this approach is probably the most likely to work.

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You can go to chrome://history/older and Make sure 'Older' is selected. Then you can press F12 to go to developer tools, find "Console" tab and paste and run this code (and wait a while):

var fun = ()=>{setTimeout(() => {document.querySelectorAll('button[title=Delete]').forEach(b => b.click()); console.log('d'); fun();}, 1); }; fun();

It clicks the "Delete" button for each item on the list.

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