This might help you Ok... so I evidentally had a collection that was broken and needed to be detached and deleted before I could do the upgrade. This required me to re-install TFS2010, restore from my backup, detach and delete the offending collection, and then go through the upgrade again.
tfs 2010 with an upgrade visual studio 2012 want to download a Deploy.wdproj that was deteled with the last upgrade
it helps some times According to your description and error message, this seems due to the project that was deleted from source control but still referenced in the .sln. The .sln was not aware of this. Please checkout the .sln file, and update the reference. Another solution is unbinding and binding again the solution file.
TFS 2010 Upgrade to TFS 2013 - Can Window Server 2019 Standard Support the Upgrade?
like below fixes the issue I agree with Daniel, please follow the documentation exactly. Since you can upgrade from TFS 2010 --> TFS 2012.3 --> TFS 2019, or from TFS 2010 --> TFS 2013.5 --> TFS 2019, you could consider trying to upgrade from TFS 2010 to TFS 2012.3 on the same Windows Server 2008 R2 Enterprise server, and then migrate to Windows Server 2019 Standard edition when upgrade to DevOps Server 2019.1.1(TFS 2019.1.1).
When configuring TFS 2010, I receive an error: "KB2580221 does not apply, or is blocked by another condition on you