Toss squash with olive and roast on baking sheet in 400 degree oven for about 40 minutes, tossing and moving around occasionally to evenly cook.
Meanwhile, in a medium sized pot, heat chicken broth and over low heat.
In a medium sized heavy bottom stockpot or dutch oven, saute onion, garlic, and sage in butter over medium high heat until lightly brown, 5-6 minutes.
Add rice and stir for 1 minute. You want rice to get slightly browned.
Add wine and stir until liquid is absorbed, approximately 2 minutes.
Add ½ cup of stock and continue stirring until liquid is absorbed. Continue to add stock mixture, ½ cup at a time, stirring until liquid is absorbed, until all liquid has been added to rice, approximately 30 minutes.
Turn off heat. Add roasted squash, the shredded cheese, and salt and pepper to taste. Stir to combine and allow to rest. Serve hot.