I just deployed my new MVC site to our test server.  It's IIS 6, and I finally got all the routing and content URL stuff working...well almost.  I am using the JQuery date picker, which uses CSS for the calendar image.  I have the following in a CSS class.

background: url(../../Content/Images/calendar.png) no-repeat;

Before I discovered this issue, It had discovered that "../../" is not treated as I expect.  I found this solution (Url.Content method), which works for view pages. However, obviously I cannot use that method in CSS.   I tried to solve it with routing per this post.  I tried by adding this to my main route: 

Constraints= new RouteValueDictionary(new { id = "^(?!Content).*" }

Constraints= new RouteValueDictionary(new { id = "(?!Content).*" }

Constraints = new RouteValueDictionary(new { id = "^(?!Content).*" })