From your description, it seems like you would need 2 custom post types, one for the list of winners page and one for the individual winners.
On the list of winners page type you can select which taxonomies you want to show (2009, Category). Then you can create a template that takes those taxonomy values and uses them to create a custom loop to display those Winners with the specific taxonomy values.
On the winners custom post type you have the taxonomies you’ve already listed and you create a template that will be used for all the winners.
For the landing page, depending on how you want it done you could just create page template or do something more complicated like have links automatically generate for you to each Year page that you created.
This way each year you create a listing page and select the categories you want it to show through the admin so it will be easy for non technical people to create lists of winners by year and cateogry.
Hope that helps