Rinse cherry tomatoes; pull off stems. Using sharp knife, cut cone-shaped core from stem end of each. Spoon out center of each tomato using small spoon. Drain tomatoes upside down on paper toweling.
Cut up cream cheese into bowl. Add Cheddar, milk, garlic, cumin, cayenne, salt and pepper; mash with fork. Spoon into pastry bag fitted with large plain tip; pipe into tomatoes. Or use a spoon.