Heat the oven to 450 degrees F, and line a baking sheet with parchment paper or lightly greased foil.
Cut the cabbage into quarters from top to stem end, and then slice the bottom of each quarter at an angle to remove the stem. Leave most of the core, as it will help to keep the wedges in tact. (The core will also soften when roasted and taste great.) Cut each quarter in half (top to stem end again) so you have eight equal wedges.
Place the wedges on the prepared baking sheet. Brush or spray both sides lightly with the oil, and then sprinkle both sides with salt and pepper.
Cut each slice of bacon into strips and drape over the cabbage wedges. (For more bang for the buck, I cut the bacon in half and then slice those pieces in half again, only lengthwise this time, to produce four narrow strips.)
Roast the bacon-covered wedges for 15 minutes. Remove from the oven and carefully flip the wedges.****
Return to the oven, and cook for 10-15 minutes more or until the cabbage is tender, the edges are a little crispy, and the bacon is cooked. If after 30 minutes of cooking the edges are not browned enough to suit your taste, continue cooking in 5-minute increments until the wedges are cooked to your liking. Serve immediately.
Store any leftovers, covered, in the refrigerator and gently reheat before eating.