I was afraid of that ....
The other plugins (enabled) I am using are (in order from top to bottom):
NoOverlap
Redirector
EmailNotify
DeleteOld
I just tried the scenario above again and as long as the date that does not cause the overlap problem is listed first (ie 9th, 20th 27th) the overlap occurs. If I change it around and enter the dates where the first one is causing the overlap (ie 20th, 27th, 9th) the Overlap plugin works as expected and does not allow the entry.
Not sure if it matters, but the event that is getting stepped on (Event 1) was entered as a recurring event. Also I am using a slightly modified version of the dayspan template but I'm not sure how likely that is the cause. The overlap either occurs (or doesn't) right after the save button is hit on the schedule. If the overlap occurs, redirector takes me right back to thte calendar with the overlapping event added. If the overlap does not occur, I get the error message that another event has been scheduled at the same time in the schedule event entry form.
Hope this helps some -
Keith