I’m managed to divert the old blog posts (that are went missing because of the blog upgrade, but are still listed by search engines) to the correct locations.
The old blog indexed the posts by date, however WordPress indexes via a unique post id (e.g. 1 for the first post, 2 for the next, etc), so I wrote a little bit of code that searches the old blog database table using the date (provided in URL) from the result it pulls out the post’s title and uses that data to search the WordPress blog database table for the correct post id. Once that is found the PHP Header command is used to 301 redirect the page to correct WordPress page and update the search engine.
Who said I wouldn’t need any PHP/MYSQL skills when I moved to WordPress?