Program.cs

using System;
using System.Collections.Generic;
using System.Linq;
using System.Text;
using System.Threading.Tasks;

namespace ExploreDictionaryListComparison
{
    public enum ServerConnection
    {
        SERVER_1= 0,
        SERVER_2 = 1
    }

    class Program
    {
        static void Main(string[] args)
        {

            Dictionary<ServerConnection, List<Servers>> servers = new Dictionary<ServerConnection, List<Servers>> { };

            var enumKeys = (ServerConnection[])Enum.GetValues(typeof(ServerConnection));

            foreach (var item in enumKeys)
            {
                if (!servers.Keys.Any( key => servers.ContainsKey(key)))
                {
                    servers.Add(ServerConnection.SERVER_1,
                                 new List<Servers> { new Servers { Id = Guid.Parse("ccebda07-437a-4e8d-a2a6-c8d0c31138a3") }, new Servers { Id = Guid.NewGuid() } });
                }
                else
                {
                    var values = servers.Values;

                    bool meron = values.ToList().Any(y => y.Any(x => x.Id.ToString().Contains("ccebda07-437a-4e8d-a2a6-c8d0c31138a3")));




                }

            }

         




        }
    }
}