Pineapple upside-down cake

Pineapple upside-down cake

Preparation time

30 mins to 1 hour

Cooking time

30 mins to 1 hour


Serves 12

This posh take on a Seventies’ classic brings a retro dish bang up to date. Just add friends.

By Tom Kerridge
From Tom Kerridge’s Best Ever Dishes


For the pineapple sugar syrup

  • 1 ripe pineapple, peeled using a sharp knife, eyes and core removed, flesh cut into 1.5cm/½in rings
  • 200g/7oz caster sugar
  • 1 vanilla pod, split lengthways, seeds scraped out with a knife and reserved for the cake (see below)
  • 1 cinnamon stick
  • 2 star anise
  • 2 bay leaves

For the topping

  • 150g/5½oz butter, softened, plus extra for greasing
  • 150g/5½oz soft dark brown sugar
  • 100g/3½oz pitted dates, chopped
  • 3 tsp cracked black peppercorns
  • 50ml/2fl oz dark rum (optional)

For the cake

  • 200g/7oz butter, plus extra for greasing
  • 200g/7oz soft brown sugar
  • 100g/3½oz self-raising flour, sifted
  • 2 tsp baking powder
  • 4 free-range eggs, beaten
  • reserved vanilla seeds (from the sugar syrup)
  • 50ml/2fl oz dark rum (optional)

For the toffee sauce

  • 75g/2½oz butter
  • 100g/3½oz soft brown sugar
  • 30ml/1fl oz dark rum

For the coconut cream (optional)

  • 2 x 160ml/5½fl oz cans coconut cream, chilled in the fridge overnight
  • 2 tbsp caster sugar
  • 1 lime, finely grated zest only, to serve


  1. Lightly grease a 24cm/9½in square cake tin with butter. Line the base and sides with baking parchment.
  2. For the pineapple sugar syrup, use two cookie cutters to make the outside edges and inside edges of each pineapple ring a uniform shape, alternatively trim them using a sharp knife. You need 4-5 pineapple rings.
  3. Pour 500ml/18fl oz water into a large saucepan and add the caster sugar, vanilla pods, cinnamon stick, star anise and bay leaves. Bring to the boil, then add the pineapple rings and reduce the heat until the mixture is just simmering. Continue to simmer for 15-20 minutes, or until the pineapple is tender. Set the pan aside until the contents have completely cooled.
  4. For the topping, put the butter and dark brown sugar in a large bowl. Using an electric whisk, beat them until fluffy, then stir in the dates, black peppercorns and the rum (if using).
  5. Drain the cooled pineapple rings and arrange them into the bottom of the cake tin. Spread the topping mixture over the pineapple rings in an even layer.
  6. For the cake, preheat the oven to 180C/350F/Gas 4.
  7. In a clean mixing bowl, beat together the butter and sugar until fluffy using an electric whisk. Add the flour, baking powder, eggs, vanilla seeds and the rum, if using, then whisk again until just combined.
  8. Spoon the cake mixture into the cake tin and smooth the top using a palette knife. Bake for 45 minutes, or until a skewer inserted into the centre of the cake comes out clean. Remove from the oven and set aside to cool for 10-15 minutes.
  9. When cooled, turn the pineapple upside-down cake out onto a serving plate and remove the baking parchment.
  10. For the toffee sauce, melt all of the toffee sauce ingredients together in a small saucepan over a low heat. Increase the heat until the mixture is boiling, then remove the pan from the heat.
  11. For the coconut cream, in a mixing bowl, whisk together the chilled coconut cream and the caster sugar until soft peaks form when the whisk is removed.
  12. To serve, slice the pineapple upside-down cake. Place each slice onto a serving plate, then drizzle over a little toffee sauce. Place a dollop of coconut cream alongside (if using), then sprinkle over a little lime zest.

Recipe Tips

If you are pressed for time, use canned pineapple rings in juice for this recipe (you will need 4-5 rings) and steep them in the spiced sugar syrup.