Line two muffin cups with plastic wrap. Divide ice cream between cups. Press a chocolate-covered cherry into each; smooth ice cream over cherries. Freeze overnight or until firm.
Invert ice cream onto a waxed paper-lined plate; remove and discard plastic wrap. Spread jam over ice cream; freeze until firm.
Place a wire rack over a sheet of waxed paper. Using a fork, transfer ice cream to rack. Pour ice cream topping over each to coat. Transfer to dessert plates; freeze until serving. Serve with whipped cream and chocolate syrup.