Preheat oven to 425 degrees. Spread the pumpkin seeds on a large rimmed sheet. Toast, tossing once, until just beginning to dark about 4 minutes. Let cool. Coarsley chop; set aside.
Toss squash in 1 tablespoon olive oil on a large rimmed baking sheet; season with salt and pepper. Roast squash, turning occasionally, until golden brown, and tender 35-40 minutes.
When squash has been roasting for 30 minutes, heat 1 tablespoon oil in a large heavy skillet over medium-high heat. Season pork chops with salt and pepper and cook until brown, approximately 10-12 minutes, depending upon thickness. Turn and cook pork until cooked through.
Whisk garlic, 3 tablespoons chopped cilantro, 2 tablespoons lime juice, reserved toasted pumpkin seeds, and remaining 3 tablespoons oil in a small bowl to combine. Season vinaigrette with salt, pepper, and more lime juice, if desired.
Divide squash and pork among plates; spoon vinaigrette over. Top with cilantro leaves.