Heat oven to 180C/160C fan/gas 4.
For the topping, beat 50g softened butter and 50g light soft brown sugar together until creamy. Spread over the base and a quarter of the way up the sides of a 20cm round cake tin. Arrange 7 pineapple rings on top (reserving the syrup for later), then place 7 glacé cherries in the centres of the rings.
Place 100g softened butter, 100g golden caster sugar, 100g self-raising flour, 1 tsp baking powder, 1 tsp vanilla extract and 2 eggs in a bowl along with 2 tbsp of the reserved pineapple syrup. Using an electric whisk, beat to a soft consistency.
Spoon into the tin on top of the pineapple and smooth it out so it’s level. Bake for 35 mins. Leave to stand for 5 mins, then turn out onto a plate. Serve warm with a scoop of ice cream.