Are there any concurrency debugging tools for C#.NET in VS2010
Within Visual Studio 2010 (not sure which editions exactly) you can create a new profiling session with the "Concurrency" option. This should detect the deadlocks you're looking for. You can then profile a unit test to automate your many runs.
Couldn't find many images of the results but here's an example
(source: microsoft.com)
Another tool is from Microsoft Research only, you can download it from Codeplex - chesstool.codeplex.com. It supports .Net 4.0 libraries, next version of Chess, but I don't know you are able to use it.