DRAIN 1 can (14 fl oz / 398 mL) peach slices and mandarin orange segments, reserving liquid. Set orange segments aside for later use.
PREPARE 1 pkg. (4-serving size) Jell-O Vanilla Instant Pudding according to package directions, reducing milk to 1-1/2 cups. Gently stir in 2 cups thawed Cool Whip Topping. Cut 1 (298 g) pound cake into 1/2-inch slices.
CUT rounds from pound cake slices using a cookie cutter. Place 1 cake slice in each individual glass dessert dish. Pour a little of the reserved mandarin orange liquid over each cake slice; top with layers of orange segments and pudding mixture. Repeat all layers. Top with additional whipped topping.