Rx is indeed a good fit for this problem IMO.
IObservables can't 'OrderBy' for obvious reasons (you would have to observe the entire stream first to guarantee the correct output order), so my answer below makes the assumption (that you stated) that your 2 source event streams are in order.
It was an interesting problem in the end. The standard Rx operators are missing a GroupByUntilChanged that would have solved this easily, as long as it called OnComplete on the previous group observable when the first element of the next group was observed. However looking at the implementation of DistinctUntilChanged it doesn't follow this pattern and only calls OnComplete when the source observable completes (even though it knows there will be no more elements after the first non-distinct element... weird???). Anyway, for those reasons, I decided against a GroupByUntilChanged method (to not break Rx conventions) and went instead for a ToEnumerableUntilChanged.
Disclaimer: This is my first Rx extension so would appreciate feedback on my choices made. Also, one main concern of mine is the anonymous observable holding the distinctElements list.
Firstly, your application code is quite simple:
    public class Event
    {
        public DateTime Timestamp { get; set; }
    }
    private IObservable<Event> eventStream1;
    private IObservable<Event> eventStream2; 
    public IObservable<IEnumerable<Event>> CombineAndGroup()
    {
        return eventStream1.CombineLatest(eventStream2, (e1, e2) => e1.Timestamp < e2.Timestamp ? e1 : e2)
            .ToEnumerableUntilChanged(e => e.Timestamp);
    }
Now for the ToEnumerableUntilChanged implementation (wall of code warning):
    public static IObservable<IEnumerable<TSource>> ToEnumerableUntilChanged<TSource,TKey>(this IObservable<TSource> source, Func<TSource,TKey> keySelector)
    {
        // TODO: Follow Rx conventions and create a superset overload that takes the IComparer as a parameter
        var comparer = EqualityComparer<TKey>.Default;
        return Observable.Create<IEnumerable<TSource>>(observer =>
        {
            var currentKey = default(TKey);
            var hasCurrentKey = false;
            var distinctElements = new List<TSource>();
            return source.Subscribe((value =>
            {
                TKey elementKey;
                try
                {
                    elementKey = keySelector(value);
                }
                catch (Exception ex)
                {
                    observer.OnError(ex);
                    return;
                }
                if (!hasCurrentKey)
                {
                    hasCurrentKey = true;
                    currentKey = elementKey;
                    distinctElements.Add(value);
                    return;
                }
                bool keysMatch;
                try
                {
                    keysMatch = comparer.Equals(currentKey, elementKey);
                }
                catch (Exception ex)
                {
                    observer.OnError(ex);
                    return;
                }
                if (keysMatch)
                {
                    distinctElements.Add(value);
                    return;
                }
                observer.OnNext( distinctElements);
                distinctElements.Clear();
                distinctElements.Add(value);
                currentKey = elementKey;
            }), observer.OnError, () =>
            {
                if (distinctElements.Count > 0)
                    observer.OnNext(distinctElements);
                observer.OnCompleted();
            });
        });
    }