The fourteenth season of the television series aired during October and November of 2010 in the UK and between November 2010 and January 2011 in the US. There was a total of twenty episodes.
- Thomas' Tall Friend - Thomas must deliver a giraffe to the Animal Park, but is too excited to wait for its keeper.
- James in the Dark - James refuses to wear an old fashioned head lamp at night and picks up Farmer McColl, Farmer Trotter, and their animals instead of Alicia Botti.
- Pingy Pongy Pick Up - Emily must pick up the Sodor United football team's kits.
- Charlie and Eddie - Edward tries to show Charlie that he is a fun engine instead of delivering Sir Topham Hatt's car to a mechanic.
- Toby and the Whistling Woods - Thomas and James help Toby get through the Whistling Woods.
- Henry's Health and Safety - Henry becomes so concerned about safety, he interferes with Percy's jobs.
- Diesel's Special Delivery - Diesel swaps his dull load of slate for a haul of shiny red apples and bright flowers in order to please Sodor's schoolchildren.
- Pop Goes Thomas - Thomas is amused by the popping sounds coming from his load of lemonade, but when he delivers the cargo, he discovers that the bottles are empty.
- Victor Says Yes - Victor bites off more than he can chew when he agrees to fix many of Sodor's engines on the same day.
- Thomas in Charge - The Railway Inspector pays a visit to Sodor, but Thomas' ambitious plans to impress him lead to chaos.
- Being Percy - Percy decides to imitate Gordon in order to get the other engines to take notice of him.
- Merry Winter Wish - Thomas delivers the Star of Knapford, a festive light that makes wishes come true.
- Thomas and the Snowman Party - Thomas must find a special hat for a snowman before the party can begin.
- Thomas' Crazy Day - The Fat Controller enlists Thomas to teach the silly Logging Locos how to be useful, but he has already promised to play a game with Percy.
- Jumping Jobi Wood! - Thomas is ordered to collect some precious Jobi wood from Misty Island, but chaos ensues when Old Wheezy starts throwing the logs around.
- Thomas and Scruff - Thomas tries to clean a new engine named Scruff, but as soon as he knows he's getting a wash, he runs off in terror.
- O the Indignity - Gordon is put in charge of Whiff's Waste Dump on "Clean Sodor Day".
- Jitters and Japes - Thomas takes Dowager Hatt on a slow tour of Misty Island, but the Dowager wants to have a more exciting trip.
- Merry Misty Island - Bash, Dash, and Ferdinand prepare for the first ever Misty Island Christmas party.
- Henry's Magic Box - Henry helps Sir Topham Hatt prepare a secret holiday surprise.
- Bash and Dash
- 'Arry and Bert
- Ol' Wheezy
- Sir Topham Hatt
- Dowager Hatt
- Stephen Hatt
- Bridget Hatt
- Alicia Botti
- Mr. Bubbles
- A Dockyard Workman
- Annie and Clarabel (do not speak)
- Bertie (does not speak)
- Lady Hatt (does not speak)
- Sodor Brass Band (do not speak)
- The Mayor of Sodor (does not speak)
- Farmer McColl (does not speak)
- Farmer Trotter (does not speak)
- Stanley (cameo)
- Henrietta (cameo)
- Jem Cole (cameo)
- The Duchess of Boxford (cameo, mentioned)
- Mr. Percival (cameo)
- The Photographer (cameo)
- The Teacher (cameo)
- The Maithwaite stationmaster (cameo)
- The Knapford stationmaster (cameo)
- The Duke of Boxford (mentioned)
- Father Christmas (mentioned)
UK and AUS
- Michael Angelis as the narrator
- Ben Small as Thomas, Toby, and Ferdinand
- Keith Wickham as Percy, James, Gordon, Henry, Edward, Salty, Harold, Sir Topham Hatt, Dash, Captain, Dowager Hatt, Whiff, and Mr. Bubbles
- Matt Wilkinson as Victor, Charlie, Bash, Spencer, Rocky, Cranky, Kevin, the Island Inspector, the Dockyard Worker, and the Blonde-haired Boy
- Teresa Gallagher as Emily, Mavis, Rosie, the laundry lady, the Ginger-haired Boy, and the schoolchildren
- Togo Igawa as Hiro
- Kerry Shale as Diesel, 'Arry, and Bert
- Jules de Jongh as Alicia Botti
- Michael Brandon as the narrator, Diesel, and Mr. Bubbles
- Martin Sherman as Thomas and Percy
- Kerry Shale as Sir Topham Hatt, Henry, Gordon, James, Bash, Scruff, Harold, Kevin, 'Arry, Bert, and the Railway Inspector
- William Hope as Edward, Toby, Whiff, Dash and Rocky
- Jules de Jongh as Emily, Mavis, Rosie, Alicia Botti, the laundry lady, and the schoolchildren
- Togo Igawa as Hiro
- Keith Wickham as Salty, Captain, and Dowager Hatt
- David Bedella as Victor
- Glenn Wrage as Spencer, Charlie, Ferdinand and Cranky
- Although originally broadcast in 2010, episodes one - eight, seventeen, and twenty have a copyright of 2009.
- This was Sharon Miller's last season as creative producer.
- This was Jo Jordan's first season as creative producer.
- This is the third season not to feature the Skarloey Railway engines since their debut, following the eighth and thirteenth season.
- Whiff's whistle now budges up and down when he uses it.