- 2013 (White bordered wheels; later models had fully black wheels)
- 2018 (Wooden windshield and canopy, no paint in various spots, plastic middle section to hold figure, standard road wheels)
- Winston's first Prototype had no facial details.
- He was originally planned to be released in 2012, but his model was delayed due to Fisher-Price buying the Thomas Wooden Railway range and was released in 2013.
- The Sir Topham Hatt inside of Winston has red facial details.
- Winston's 2013-2017 model had specially molded wheels to better match the ones he has in the television series. His 2018 model gains the standard wheels that every road vehicle has.