Preheat the oven to 200°C conventional (180°C fan-forced).
On a baking tray, arrange the cherry tomatoes and whole garlic cloves. Drizzle with 2 tablespoons of the olive oil and season well. Roast for 25 minutes.
Meanwhile, in a medium–large pot, heat the remaining 3 tablespoons of olive oil over medium heat. Add the smashed garlic cloves and canned tomatoes, along with the roasted tomatoes and garlic. Season with salt and pepper.
Add the chicken stock to the pot, bring to the boil, then turn down to a simmer for 10 minutes. Add the basil and bread. Simmer, stirring occasionally, for 10–15 minutes.
Serve with a drizzle of olive oil, basil leaves and parmesan.