Possible to use AutoMapper to map one object to list of objects?

You will need these three mapings with one custom converter:

Mapper.CreateMap<Event, EventDTO>(); // maps message and event id
Mapper.CreateMap<EventLog, EventDTO>(); // maps system id and user id
Mapper.CreateMap<EventLog, IEnumerable<EventDTO>>()
      .ConvertUsing<EventLogConverter>(); // creates collection of dto

Thus you configured mappings from Event to EventDTO and from EventLog to EventDTO you can use both of them in custom converter:

class EventLogConverter : ITypeConverter<EventLog, IEnumerable<EventDTO>>
{
    public IEnumerable<EventDTO> Convert(ResolutionContext context)
    {
        EventLog log = (EventLog)context.SourceValue;
        foreach (var dto in log.Events.Select(e => Mapper.Map<EventDTO>(e)))
        {
            Mapper.Map(log, dto); // map system id and user id
            yield return dto;
        }
    }
}

Sample code with NBuilder:

var log = new EventLog {
    SystemId = "Skynet",
    UserId = "Lazy",
    Events = Builder<Event>.CreateListOfSize(5).Build().ToList()
};

var events = Mapper.Map<IEnumerable<EventDTO>>(log);

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