Preheat the oven to 180C/350F.
Slice the tip off the garlic bulb to expose the cloves. Drizzle with oil then wrap in foil. Place on a baking tray then pop in the oven for 15 minutes.
Meanwhile, slice the potatoes into ¾" cubes. Combine in a bowl with the seasoning and oil.
Once the garlic has roasted for 15 minutes, spread the potatoes out on the tray and place in the oven for a further 40-45 minutes, or until the garlic is very soft and golden, with the potatoes crisp on the outside and soft through the centre. Just be vigilant throughout and if one finishes before the other, remove from the oven whilst the other continues cooking. If the potatoes are struggling to crisp, raise the temp to 200C/400F AFTER you've taken the garlic out.
For the steaks, pat them dry with kitchen roll and generously season both sides with salt and pepper.
Add a large cast-iron or heavy-based pan over high heat. Once the pan is very hot, add the oil and leave for 5-10 seconds. Add the steaks and leave undisturbed for 2 minutes. Flip them over and fry for another minute, then add the butter, garlic cloves, rosemary and thyme. Baste the steaks for a further minute then remove and rest them to one side, leaving everything else in the pan.
Lower the heat to medium and add the shallot to the leftover fat. Fry until soft and golden (make sure it doesn't burn) then pour in the wine. Use your wooden spoon to deglaze the pan and allow the wine to simmer and reduce until almost completely evaporated. Remove the garlic, rosemary and thyme.
Pour in the stock, cream and Worcestershire sauce, then squeeze in the roasted garlic. Give it a good stir and simmer, stirring frequently, until the sauce begins to thicken. It will thicken, just keep simmering and stirring away (approx 7-10 minutes). When the sauce is nearly done, stir in the resting juices from the steak, then season to taste with salt and pepper.
Serve the steak with the sauce drizzle on top alongside the potatoes (there will be plenty of sauce!).