In theory, yes. But the upgrade routines assume a standard Confluence with no tweaks, and there aren't really a lot of those around! In practice: Read the release notes for each big version (5.1, 5.2, 5.3 etc) in case there's anything that might affect you. Then do the same for ALL user-installed plugins you've got and want to keep. Then, set up a test system and test it!
You can also give a try to the manual procedure of the upgrade, once you have the upgrade path in mind:
(!) Before jumping to the standard procedures form a upgrade, we suggest the users to check the plugin compatibility with the next versions :https://confluence.atlassian.com/display/UPM/Checking+Add-on+Compatibility+with+Application+Updates. With that in mind, we can start the upgrade process by following the standard procedures:
Hope it helps ya!
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