Preheat the oven to 190°C/Gas 5. Cut the squash into slim wedges and scoop out the seeds. Put the squash wedges into a roasting tray, skin side down. Scatter the bashed garlic cloves over the squash. Roughly crush the sage leaves, if using, in your hands to release the flavour and strew these over too. Trickle the oil all over everything and season well with salt and pepper. Roast for 40 minutes, checking after 25 minutes to see if any of the sage leaves are starting to look charred; if so take them out, but retain.
Meanwhile, to make the chilli oil, heat the extra virgin olive oil, chilli, paprika and garlic gently together in a small saucepan over a low heat for 3–4 minutes. You want the oil barely fizzing – just hot enough to infuse the chilli. Set aside until needed.
Shortly before the roasting time is up, peel, quarter and core
the apples. Cut each quarter in half. When the squash has had
40 minutes, remove the sage if you haven’t already and add the apples to the tray. Stir everything around a bit, then return to the oven for a further 20 minutes, by which time the squash should be tender and caramelised and the apples collapsing.
Squeeze the roasted garlic cloves out of their skins into a blender (omit any that are a bit burnt). Add the apples. Scrape the squash flesh away from the skin and add this too. Add any oily juices left in the tray and a few of the sage leaves. Pour about 400ml stock into the blender and blitz to a thick, creamy purée. Add more stock as you like, to achieve a consistency you are happy with. The amount you need will vary depending on the variety of squash: butternut is quite wet, but many other squashes have drier flesh. Transfer to a saucepan and reheat. Add salt and pepper to taste.
Serve in warm bowls, topped with a generous trickle of the chilli oil. You can include a few fragments of chilli and garlic with the oil if you like, or not; it’s up to you.
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