Win, Lose or Draw is the fourth episode of the second season.
The kids enter a drawing contest. Becky does not like the way her picture looks, so she asks Mr. Conductor to use his magic to draw her a nicer picture. Schemer steals Billy's ink to draw a self-portrait, but finds out that it is disappearing ink. At the end, Becky learned to appreciate her original drawing and she won third prize.
- Mr. Conductor
- Stacy Jones
- Billy Twofeathers
- Dan Jones
- Kara Cupper
- Barton Winslow
- Schemer's Mother (mentioned)
- Thomas (mentioned)
- Gordon (mentioned)
- Percy (mentioned)
- City of Truro (not named; mentioned)
Jukebox Band Segment Song
- Arkansas Traveller
- In the Fox Family Channel version, many scenes were mixed around or edited out.
- The scene where Becky tells Kara her drawing isn't ready was edited out.
- The scene where Schemer "borrows" Billy's special ink was seen earlier in the episode.
- The scene where Becky asks Mr. Conductor to make a better picture of Stacy was edited out.
- After the commercial break, the scene where Schemer asks the kids to make a picture of himself was edited out.
- Tito's magic piano story was edited out.
- The Jukebox Band song was edited out.
- The part where Mr. Conductor tells Becky that he was going to Mt. Careful to jump over molehills was shortened.
- In the Nick Jr. version, during "Double Trouble", the scene of Toby taking Annie and Clarabel is cut out.
- This is Barton Winslow's first appearance.
- Gerry Parkes joins the cast.
- You'll notice that Barton's manner of speaking always switches to 1950s slang whenever he puts on his leather jacket.