Windows 2008 R2: Unable to upgrade MySQL 5.5.58
You have to follow the upgrade path and follow the upgrade insructions
From 5.5 to 5.6
https://dev.mysql.com/doc/refman/5.6/en/upgrade-paths.html
rom  5.6 to 5.7
https://dev.mysql.com/doc/refman/5.7/en/upgrade-paths.html
And finally from 5.7 to 8.0
https://dev.mysql.com/doc/refman/8.0/en/upgrade-paths.html
Ther you will find also the upgrade instructions