Preheat oven to 400 degrees. Line a baking sheet with aluminum foil. Toss the chunks of squash with the olive oil in a large bowl. Spread out on prepared baking sheet. Season with salt & pepper. Bake 20 minutes, flip, then bake an additional 15 minutes.
Heat nonstick skillet over medium-high heat. Cook pancetta until crisp. Drain on a paper towel-lined plate. Add the panko to the skillet and cook until toasted (about 2 minutes). Remove the panko and set aside. Heat the butter in the skillet until melted. Add half of the sage and continue to cook until butter is browned. Turn off heat. Crumble the pancetta when cool enough to handle.
Bring a large pot of salted water to a boil. Cook the penne according to package directions.
Drain pasta and place in a large serving bowl. Toss with remaining sage, browned butter, crumbled pancetta, panko, and roasted squash.