Preheat the oven to 190ºC and very lightly grease a 28 x 23 cm (11 x 9 inch) baking tray with oil.
In a small bowl, whisk together the olive oil, syrup, salt, and pepper until emulsified. Set aside.
Trim the top off of the acorn squash and slice it in half lengthwise. Remove and discard the seeds. Turn the squash on its flat side and slice each half into 4 equal pieces.
Wrap one bacon slice completely around each of the 8 pieces of squash.
Place each bacon-wrapped squash slice in the baking tray, spread evenly apart. Brush the oil and maple syrup mixture over each piece of squash, being careful to get it on the sides and in all the crevices. Sprinkle over half of the red chilli slices.
Bake the squash for 35-50 minutes, carefully flipping the slices half way through the cooking time. You’ll know they’re done when a fork can be easily inserted into the squash and the bacon is golden and crisp.
Remove the tray from the oven and allow the slices to rest for 5 minutes before topping with the remaining fresh chilli and a sprinkle of goat’s cheese. Serve immediately.