Arrange pickle rounds between two pieces of paper towels to absorb moisture.
In a medium sized bowl, whisk 1/4 cup of flour, the cornstarch, Italian seasoning, Cajun seasoning and cayenne pepper together. Stir in the club soda.
In a separate bowl, put the remaining 1/2 cup of flour.
Heat 1/2 inch of oil in a large skillet over medium heat.
Dredge pickles in the flour, then the wet batter. Drop pickles into the hot oil. Fry until golden brown on both sides. Remove to a wire rack positioned over paper towels.
Combine the dipping sauce ingredients in a small bowl. Serve the dipping sauce alongside the warm fried pickles.