Preheat oven to 200°C/400°F. Line a rimmed baking tray with parchment paper. Arrange the squash over the baking sheet and drizzle is 1 tsp of olive oil and season generously with salt and pepper. Flip the squash and drizzle with another teaspoon of olive oil and season with more salt and pepper.
Move to the oven and roast until the squash is golden, very tender and a fork inserted into the flesh offers very little or no resistance - approximately 25 to 30 minutes. Allow the squash to cool until just cool enough to handle and use the flat side of a knife to mash the garlic cloves.
Remove the peels from the squash and add to a large mixing bowl along with the mashed garlic cloves. Add in the butter, maple syrup, soy sauce, ginger, garam masala, turmeric and cayenne pepper.
Use a potato masher to puree the squash and incorporate the other ingredients. Serve immediately.