Preheat oven to 375 degrees. Place broccoli into a large bowl; drizzle with olive oil and sprinkle with Italian seasoning and salt. Toss well to evenly coat and then set aside.
Boil the cubed squash until it is fork tender, about 12-15 minutes. Drain well.
Mash the squash, then add the salt, nutmeg, ginger, cinnamon, allspice, and milk. Stir well to combine.
Heat a saute pan over medium. Add the squash mixture; cook and stir for 3-5 minutes, allowing the mixture to thicken slightly and the moisture to evaporate.
Place just under 2 teaspoons of filling in the middle of each wonton wrapper.
Dip your fingers into a clean bowl of water and moisten the edge around the bottom half of your wonton wrapper.
Dry your fingers, grab the top center of the wonton and gently fold it down to the bottom. Working from the center point outwards, seal in the filling. Try to avoid getting extra air in the ravioli.
Place the completed ravioli on a floured surface while you finish the others. Once finished, place the broccoli onto a baking sheet and roast in the preheated oven for 15 minutes or until crisped as desired.
Boil a pot of water. Carefully add the ravioli one at a time, then reduce the heat to medium.
Simmer the ravioli for 5-7 minutes. They are done when they float to the surface.
Use a slotted spoon to gently remove the ravioli. Avoid dumping them into a colander because they will likely break.
Tear or chop the sage leaves.
In a small saucepan melt the butter over medium-high heat, stirring or shaking the pan occasionally. Once the butter begins to foam, add the sage.
When the foaming subsides, the butter will begin to darken and smell nutty. Remove from the heat.
Plate the ravioli and drizzle with the sage brown butter sauce. Serve with roasted broccoli.