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Introduction:

The purpose of writing this post on what SQL version supported with what Windows version is because one of onshore client wanted to migrated its database servers from SQL 2014 to SQL server 2019 version. Yes, it is rolling upgrade with 2 phase involved and it was very much crucial to cut down double work for windows upgrade hence, we suggested them to give us a parallel environments with OS 2019 installed on them and lets migrated to SQL 2014 first then SQL 2019. Here is the list of SQL supporting on OS versions.

Does backup of SQL 2008r2 support restoring directly on SQL server 2019?

Backup and restore. A backup taken on SQL Server 2008 (10.0.x) and later, can be restored to SQL Server 2019 (15.x) without changing its compatibility level, as long as the database backup has a compatibility level of 100 or higher.

Databases with a compatibility level of 90, including backups taken on SQL Server 2005 (9.x), are automatically upgraded to a compatibility level of 100 when restored to SQL Server 2019 (15.x)

Please refer Microsoft link for this

Happy learning..!