using System;

using System.Collections.Generic;

using System.Linq;

public class Program

{

    public static void Main()

    {

        var scripts = new List<Script>()

        {

            new Script { Database = "master", File = "sql_master" },

            new Script { Database = "myDB", File = "sql_sameGroup1" },

            new Script { Database = "myDB", File = "sql_sameGroup2" },

            new Script { Database = "myDB", File = "sql_sameGroup3" },

            new Script { Database = "myDB", File = "sql_special" },

        };

        var grouped = scripts.GroupBy(script => new { script.Database, IsSqlSpecial = script.File is "sql_special" });

        foreach (var group in grouped)

        {

            Console.WriteLine(group.Key);

            foreach (var entry in group)

            {

                Console.WriteLine($"{entry.Database} {entry.File}");

            }

            Console.WriteLine();

        }

    }

}

​

public class Script

{

    public string Database{get;set;}

    public string File{get;set;}

}