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How can I remove old content or URL from search engine (Google, Bing, and Yahoo)?
How to remove URLs from Google search results:

Prerequisite: Google webmaster tools account for the specified site, verified by either HTML Meta tag or uploading XML Verification file.

Steps:

      1. Verify your ownership of the site in Webmaster Tools.
      2. On the Webmaster Tools home page, click the site you want.
      3. On the Dashboard, click ‘Site configuration’ in the left-hand navigation.
      4. Click ‘Crawler access’, and then click ‘Remove URL’.
      5. Click ‘New removal request’.
      6. Type the URL of the page you want removed from search results (not the Google search results URL or cached page URL), and then click ‘Continue’.

warning Please Note:the URL is case-sensitive—you will need to submit the URL using exactly the same characters and the same capitalisation that the site uses.

      7. Click ‘Remove page from search results and cache’.
      8. Select the checkbox to confirm that you have completed the requirements listed in this article, and then click ‘Submit Request’.
            Read more on page removal options at Google Webmaster Central.

How to remove URLs from ‘Bing’ search results:

Prerequisite: Bing Webmaster Centre account for the specified site, verified by either HTML Meta tag or uploading XML Verification file.

Steps:
        1. Open the Bing Search Support form.
         2. Fill out the form.
                         > Primary e-mail address: provide the email that is associated with your Bing Webmaster Centre account.
                         > What type of problem do you have? – First select Content Removal Request from the drop down menu.
                         > Once ‘Content Removal Request’ option is selected, another drop-down menu will appear right bellow the first one. Select Cached page removal
                          > Enter the URL you want to remove
                          > Enter the search query/ keyword that returns that URL
                          > Fill the rest of the form.
         3. Input the Captcha entry.
         4. Click Submit.

Read more at Bing Community.

How to remove URLs from Yahoo search results:

Prerequisite: Yahoo Site Explorer account for the specified site, verified by either HTML Meta tag or uploading XML Verification file.

Steps:
      1. Sign in to Yahoo Site Explorer. Enter the URL/Path into the ‘Explore URL’ box.
      2. Locate the site in Explorer results. Notice the ‘Delete URL/Path’ button next to each URL. 
           

warning Note:When you use Site Explorer to delete a URL/Path from the Yahoo! index, it deletes that URL as well as all the sub paths listed under that URL.

      3. Click ‘Delete URL/Path’ to go to the confirmation page.The confirmation page shows the total number of sub path URLs that will be affected as a result of that Delete                URL/Path action and also displays a list those URLs.
      4. Use the input text box to edit the URL and limit the delete action to a specific sub directory.Click ‘Update’ to regenerate the list of URLs that will be affected by the                      delete action. 


        Example of deleting multiple URLs:

        Use the Delete URL/Path option to remove multiple URLs by truncating the URL string back to the trailing ‘?’ mark, then clicking the ‘Update’ button. To remove URLs              that look like this:

         http://example.com/test/index.php?test=foo&user=john

          truncate the URL back to the ‘?’ mark:

           http://example.com/test/index.php?

           Click the ‘Update’ button to regenerate the list of URLs that will be affected by the delete action.
      5. Click ‘Yes’ to delete the URL and any sub paths listed.

When you click ‘Yes’, the delete action is recorded and the ‘Actions’ page opens. The ‘Actions’ page lists all currently live actions on the site, and also includes actions made by all authenticated site owners.

When Yahoo! Applies the Delete URL/Path action, its status on the ‘Actions’ page changes from ‘Pending Delete’ to ‘In Effect’. At this point the delete action starts propagating through Yahoo index. It will usually be updated throughout the entire index within 48 hours.
Read more at Yahoo HELP