Stephen had never grown up to be controller, and has always remained as about the same age. He was amongst the boys who teased Daisy about bull's-eyes, and was also amongst the boys who teased Sir Handel about George. He and Bridget helped Toby discover an old castle. He thought that Edward was the strongest and the best, after Edward pushed Duck, Gordon, and their trains into Knapford Station. He and Bridget flew a kite, which got blown away, but Thomas, along with Charlie, Percy, Edward, and Emily retrieved it. He and Bridget later caught chickenpox, convincing Henry that engines could catch chickenpox as well.
- Season 1 - Emily Helps Out (deleted scene cameo), James and the Big Red Balloon (cameo), Rheneas' Roller Coaster (cameo), Oliver and the Snowman (not named), Fishy Troubles (cameo), Harold and the Flying Climbers (cameo), and Thomas' Three Cheers (cameo)
- Season 2 - Henry's Fire Rescue, Hiro and the Coaches (cameo), and Flying Scotsman Departs (cameo)
- Season 3 - Old Slow Coach (cameo), The New Controller (cameo), Geoffrey and the Small Engines (cameo), Bertie's Foggy Day (cameo), Snowed up Engines (cameo), and Cold Crews (cameo)
- Season 4 - Flora's Tram Coach (cameo), Duck and the Coaches (cameo), Saved by the Belle (cameo), and Oliver's Sea Rescue (cameo)
- Season 5 - The Big City Engine (cameo) and A Vintage Coach (cameo)
- Thomas and the Storm (cameo)