Yes this can be accomplished. Without knowing the specifics of your board and workflow, here is a suggestion off the top of my head: Move the won jobs into groups or boards so your dashboard can read and show the specific information you want. This can be accomplished automatically.
-Job Worth (Numbers Column)
-Won (Status Column*)
-Won Date (Date Column)
*This can be the same status column as your overall status, if you already use something like that. Just add a “Won” option.
-When Status changes to Something set Due Date to current date.
-When Status changes to Something move item to Group.*
*This could also be "move item to Board if you prefer that route.
When you win a job, it gets marked as “Won” and then the date gets set, and it moves into your specified group. Once there, you can customize your dashboard to separate them by date ranges and include values. You could technically set up the dashboard to do this without moving the items, but would mean searching for items with a Status of “Won”. I find narrowing the dashboard to groups or separate boards to be easier.
Hopefully this helps! Let me know if you have any questions.