While squash is roasting, dice bacon and cook over medium high heat in large skillet until crispy. Remove from pan and drain.
Leave just enough bacon grease in pan to lightly coat the bottom and reduce heat to low, add thinly sliced red onion and cook on low until caramelized, stirring occasionally. This should take roughly the same amount of time as your squash, if you find your onions are done before your squash simply remove pan from heat until your squash is ready.
When your onions are caramelized add the garlic to the pan and saute until fragrant (~1 minute).
Add prepared squash and bacon to the pan and season with cumin, salt and pepper to taste, stirring gently until warmed through.