Preheat the oven to 375 degrees F. In a mixing bowl, combine the ground pork, diced apple, chopped sage, onion, egg, salt, and pepper. Mix until evenly blended.
Divide the mixture into four portions and shape each into a small loaf. Place the loaves in a muffin tin or on a baking sheet lined with parchment.
Bake the meatloafs for 25 to 30 minutes until they reach an internal temperature of 160 degrees F.
While the meatloafs bake, place the cubed butternut squash in a pot and cover with water. Bring to a boil and cook for 12 to 15 minutes until the squash is fork-tender. Drain the water, then mash the squash with the olive oil, salt, and pepper until smooth.
Serve each mini meatloaf with a portion of the butternut squash mash on the side.