You can upgrade instances of SQL Server 2012 (11.x), SQL Server 2014 (12.x), SQL Server 2016 (13.x), or SQL Server 2017 (14.x) directly to SQL Server 2019 (15.x).
For SQL Server 2008, and SQL Server 2008 R2, you’ll either need to do a side-by-side upgrade, or a migration, to move to SQL Server 2019 as there is no common overlap between a supported mainstream operating system.
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