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Preheat oven to 180C/160C fan-forced. Grease a 6cm-deep, 22cm round cake pan. Line base and sides with 2 layers of baking paper.
Place pineapple slices on paper towel (you'l need 7 pineapple rings). Pat dry to remove any excess moisture. Sprinkle brown sugar over base of prepared pan. Drizzle with melted butter. Arrange pineapple over butter and sugar. Place a cherry in the centre of each pineapple ring.
Using an electric mixer, beat extra butter, caster sugar and vanilla for 5 minutes or until light and fluffy. Add eggs, 1 at a time, beating until combined after each addition. Gradually beat in flour and milk on low speed, until just combined. Spoon batter over pineapple in pan, spreading gently to level.
Bake for 55 minutes or until a skewer inserted into centre of cake comes out clean. Stand in pan for 5 minutes. Invert cake onto a baking paper-lined wire rack to cool. Serve cake warm or cold.