I've spent a bit of time in the last few days on Dimitry Vostokov's fantastic DumpAnalysis.org web site. The site is a gold mine of debugging "patterns" - situations you will commonly encounter when debugging on Windows. Dimitry has published his edited and cross-referenced blog posts in an anthology with more books to follow.
Digging around on the site you soon discover some very amusing cartoons about debugging by Narasimha Vedala. I particularly like the one about the operating table! Hope that never happens! His links page quickly takes you to some other awesome resources elsewhere on the web. In particular, Robert Kuster's thematically grouped WinDBG command reference and the very comprehensive WinDBG from A to Z!.
I also noticed Dimitry linked to some articles about debugging in the Citrix Knowledge Center. So I tapped "WinDBG" into their search box and whadya know? 96 articles referencing WinDBG covering what are in some cases very useful and general debugging topics whether you use Citrix products or not. Hats off to Citrix for that. For example, take a look at this one: Case Study: Troubleshooting Heap Corruption in Applications complete with embedded screen shots to make things more lucid. So then I popped over to my own usual stomping ground - the Microsoft Knowledge Base and also searched for "WinDBG". 104 hits! Only 8 more than Citrix! Shame on us Microsoft!
Anyway, all that reading should keep you busy for a few more days!