Sprinkle the sugar in an even layer onto the base of a large skillet. Place the skillet over medium heat and let the sugar melt.
Once the sugar has melted, arrange the figs slices on top of the sugar. Reduce the heat to low and let the figs caramelize for 2 minutes.
Add the port carefully to the pan. It will bubble violently. Leave the port to reduce over medium-low heat for 5 minutes or until it reaches a thick syrupy consistency.
Take the skillet off of the heat and transfer the figs to a plate. Spoon any extra port syrup over top and set aside to cool until ready to serve.
Roquefort Dressing
Whisk the yogurt, mayo, garlic, lemon juice, Dijon mustard, Worcestershire sauce, and salt together in a medium-sized bowl. Add the Roquefort and parsley and stir to incorporate.
Cover the dressing and transfer to the fridge until ready to serve.
Iceberg Wedge Salads
Arrange the lettuce quarters on a large platter cut-side-up. Spoon a generous amount of the Roquefort Dressing over top of the wedges and top with Port Poached Figs. Serve immediately with a knife and fork.