Preheat the oven to 350 F. Heat the grill to high.
Cut the tomatoes and cucumber into bite-sized chunks and place in a serving dish with the arugula and olives.
Mix well.
Slice the bread into eight ½ inch slices, drizzle 1 ½ tablespoons of the olive oil over the bread and season with salt and pepper.
Grill until lightly golden, and then rub each slice thoroughly with a cut side of the garlic.
Wrap loosely in foil and keep warm in the oven.
Cut the Halloumi into eight ¼ inch slices. Heat ½ tablespoon of the oil in a shallow frying pan and fry the haloumi slices for 1-2 minutes on each side, until crisp and golden brown.
Whisk together the lemon juice, oregano and remaining olive oil to use as a dressing. Season, to taste. Pour half the dressing over the salad and toss well.
Arrange the haloumi on top and drizzle with dressing.
Serve immediately with the warm garlic bread.