- Prep
- 15 min
- Cook
- 45 min
- Total
- 60 min
- Serves
- 4
Ingredients
What you’ll need — tap to tick off as you go
- 1 ¼ kg
- 4 cloves
- 3 tbsp
- 500 ml
- 1 tsp
- 1 tsp
- 1 tsp
- ½ tsp
- 100 ml
- 8 slices
- 60 g
- 200 g
Process
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Heat the oven to 200°C. Toss the halved tomatoes, chopped onion and whole garlic cloves with 2 tbsp olive oil, 1 tsp salt and 0.5 tsp black pepper on a large baking tray. Spread everything in a single layer.
Roast for 30–35 minutes until the tomato edges are charred in spots and the onions are soft and golden. The garlic should be tender enough to mash with a fork.
Scrape everything from the tray into a pot, including the sticky pan juices. Add the vegetable broth, dried oregano and sugar. Bring to a gentle simmer over medium heat and cook for 5 minutes.
Blend the soup until completely smooth with an immersion blender, or in batches in a stand blender (fill it only halfway and vent the lid). Return to the pot.
Stir in the heavy cream if using, then taste and adjust salt and pepper. Keep the soup warm over low heat while you make the sandwiches.
Butter one side of each sourdough slice. Put 50 g shredded cheddar on the unbuttered side of 4 slices, close with the remaining bread so the buttered sides face out.
Heat a large non-stick pan over medium heat. Cook the sandwiches for 3–4 minutes per side, pressing lightly with a spatula, until the bread is deep golden and the cheese has fully melted. Work in batches if needed.
Cut each grilled cheese in half and serve immediately alongside bowls of the hot tomato soup for dipping.
Kitchen notes
Kitchen notes
- The most common mistake is under-seasoning the tomatoes: roasting them with salt first concentrates their flavour and drives off water, so the soup tastes sweet rather than raw and watery.
- If your tomatoes are pale or out of season, add the sugar and an extra pinch of salt after blending; taste before serving, since the soup's balance depends entirely on the tomatoes you started with.
- Shred the cheddar yourself rather than using pre-shredded cheese, which is coated in starch and melts poorly, leaving a grainy centre.
- Cook the grilled cheese over medium, not high, heat: high heat browns the bread before the cheese melts, giving you a burnt crust and a cold middle.
Substitutions
- heavy cream→full-fat coconut milk or oat cream for a dairy-free version
- vegetable broth→chicken broth if you do not need the soup to be vegetarian
- cheddar cheese→gouda, gruyere or a dairy-free melting cheese
- sourdough bread→gluten-free sandwich bread for a gluten-free version
- fresh tomatoes→two 400 g cans whole peeled tomatoes, drained, when tomatoes are out of season
Storage & reheating
Store the soup in an airtight container in the fridge for up to 4 days, or freeze it (without the cream) for up to 3 months; thaw overnight in the fridge. Reheat gently on the stovetop over medium-low heat, stirring, until steaming, or in the microwave in 1-minute bursts. Grilled cheese is best fresh, but you can reheat it in a 180°C oven for 5-6 minutes; never microwave it or the bread turns rubbery.
FAQ
The questions we get asked most
Why is my tomato soup bitter or too acidic?
Bitterness usually comes from under-ripe tomatoes or scorched garlic. Roast the garlic whole and unpeeled if you tend to burn it, and add the 1 tsp sugar plus a small pinch of salt after blending. A tablespoon of butter or the heavy cream also rounds off sharp acidity.
Can I make this tomato soup with canned tomatoes?
Yes. Use two 400 g cans of whole peeled tomatoes, drained, and roast them on the tray with the onion and garlic for 25 minutes instead of 35. Canned tomatoes are picked ripe, so the soup often tastes better in winter than one made with fresh supermarket tomatoes.
How do I stop my grilled cheese from burning before the cheese melts?
Use medium heat and give it time, about 3-4 minutes per side. If the bread is browning too fast, lower the heat, cover the pan with a lid for 2 minutes to trap steam, and the cheddar will melt through. Shredded rather than sliced cheese also melts faster.
Can I make this soup ahead of time?
Yes, the soup keeps beautifully. Make it up to 4 days ahead, cool it quickly, and refrigerate; the flavour actually improves overnight. Reheat gently and stir in the cream at the end, since cream can split if boiled for a long time.
Why did my soup turn out watery?
Roasting is what removes excess water, so do not skip it or crowd the tray, which steams the tomatoes instead of caramelising them. If it is still thin after blending, simmer it uncovered for 10-15 minutes to reduce, or blend in a handful of cooked white beans for body.
Can I freeze tomato soup with cream in it?
Dairy cream can separate and turn grainy when frozen and reheated. Freeze the soup before adding the cream, then stir in fresh cream once it is reheated. Without cream it freezes well for up to 3 months in a sealed container.
What cheese melts best for grilled cheese?
Cheddar melts well but can be oily; mixing it with mozzarella or a little cream cheese gives a smoother pull. Avoid very dry aged cheeses, which stay solid. Low-moisture mozzarella alone tastes bland, so keep cheddar as the base.
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