Air date: October 19th, 1995 (UK), November 4th, 1996 (US)
Adapted from: Duke the Lost Engine, "You Can't Win"
Duke is feeling poorly and Stuart jokes that he and Falcon may have to keep him in order. Duke pays no attention, but when he is taking his passengers home, he starts wheezing and Falcon and Stuart have to help him. The three split up at the next station so Falcon can take Duke's train to the boat and Duke and Stuart can take Falcon's train home. Stuart is delighted, but Duke isn't quite out of steam and makes a grand effort. At the top station, a man tells his son that Duke had to help Stuart, who furiously disappears in a cloud of steam.
Tropes featured in the episode:
- Cool Old Guy: Duke tricking Stuart when he managed to push him forward with all the steam he had left and arrived at the top station.
- Ironic Echo: Stuart calls Duke a "poor old engine" as he heads the train. Then, at the end, Duke calls Stuart a "poor old engine" back.
- Title Drop: Duke says this to Stuart after getting one over him: "Poor old engine! It's no good Stuart! You can't win!"
