Preheat oven to 350°F. FOR TOPPING; melt butter in a 13 x 9-inch pan on stovetop over medium heat. Remove from heat and stir in brown sugar. Drain pineapple ring, reserving 1/2 cup juice. Fit rings tightly into bottom of pan. Tuck a cherry in center of each ring.
FOR CAKE: In medium bowl, whisk flour, baking powder, salt and nutmeg. In large bowl, beat butter and sugar for 2 minutes. Add eggs, beat until blended. On low speed, beat in 1/2 the flour mix into the egg mix. Pour in reserved 1/2 cup pineapple juice, and the milk. Beat until blended. Beat in remaining flour mix, then vanilla. Spread batter into pan.
Bake for 40 minutes or until toothpick inserted in center comes out clean. Cool cake for 10 min. Place a large baking sheet over cake, carefully invert.