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Database version 2005 failed to upgrade to 2008

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Hi there, I am trying to migration our client's database version 2005 to VPS running MS SQL 2016 Web edition.

I was trying to upgrade the database from version 2005 to 2008, then from 2008 to 2014, and so on. However, my upgrade failed when I tried attach database version 2005 in MS SQL 2008 R2 Express. I even tried to restore from the database version 2000 but still no luck. Below are the error that I encounter:

A severe error occurred on the current command.  The results, if any, should be discarded.
Converting database 'Eyecon_OMS3_GST' from version 611 to the current version 661.
Database 'Eyecon_OMS3_GST' running the upgrade step from version 611 to version 621.
Database 'Eyecon_OMS3_GST' running the upgrade step from version 621 to version 622.
Database 'Eyecon_OMS3_GST' running the upgrade step from version 622 to version 625.
Database 'Eyecon_OMS3_GST' running the upgrade step from version 625 to version 626. (.Net SqlClient Data Provider)

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For help, click: http://go.microsoft.com/fwlink?ProdName=Microsoft+SQL+Server&ProdVer=10.50.2500&EvtSrc=MSSQLServer&EvtID=0&LinkId=20476

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Server Name: AS-XP\SQLEXPRESS
Error Number: 0
Severity: 11
State: 0

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Program Location:
   at Microsoft.SqlServer.Management.Common.ConnectionManager.ExecuteTSql(ExecuteTSqlAction action, Object execObject, DataSet fillDataSet, Boolean catchException)
   at Microsoft.SqlServer.Management.Common.ServerConnection.ExecuteNonQuery(String sqlCommand, ExecutionTypes executionType)


Below are the error shown in Event Viewer:
During upgrade, database raised exception 2905, severity 25, state 1, address 02A5B0B0. Use the exception number to determine the cause.
For more information, see Help and Support Center at http://go.microsoft.com/fwlink/events.asp.


I've both restore from backup file and in-place upgrade but no luck. I got stuck in 2008, and can't move on to version 2016. Could please assist on the above matter.
Hope someone can give some advise on how to solve the above matter. Thanks.

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