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Preheat the oven to 150C fan/170C/Gas Mark 3.
Halve the tomatoes and put on baking trays cut side up. Scatter with the garlic cloves and chilli flakes. Drizzle with lots of olive oil and season well with salt and pepper. Roast for 45-60 mins, swapping the trays halfway through, until lightly caramelised.
Heat a little more oil in a pan and gently fry the shallots for 10 mins. Add the roasted tomatoes. Squeeze the insides of the roasted garlic into the pan, discarding the skins.
Add the oregano and pour in the stock. Bring to the boil, then simmer for 10 mins. Remove from the heat and cool, then chill until you are ready to serve.
Quarter the figs and toss with some salt and a drizzle of extra virgin olive oil. Spoon the soup into bowls, top with the figs and another drizzle of extra virgin olive oil and some black pepper. Serve.