Win, Lose or DrawSeason 12014 · 40 episodesEpisodes1Leo Howard and Olivia HoltContestants use drawing skills to communicate clues and win prizes. Teams are made up of kid contestants and Disney personalities. In the opener, Olivia Holt takes on Leo Howard.2Peyton List and Cameron Boyce3Dove Cameron and Joey Bragg4Laura Marano and Raini Rodriguez5G. Hannelius and Blake Michael6Garrett Clayton and Chrissie Fit7Tyrel Jackson Williams and Billy Unger8Bradley Steven Perry and Jake Short9Leo Howard and Olivia Holt10Dove Cameron and Joey Bragg11G Hannelius and Blake Michael12Peyton List and Cameron Boyce13Tyrel Jackson Williams and Billy Unger14Laura Marano and Raini Rodriguez15Bradley Steven Perry and Jake Short16Leo Howard and Olivia Holt17Garrett Clayton and Chrissie Fit18G. Hannelius and Blake Michael19Tyrel Jackson Williams and Billy Unger20Dove Cameron and Joey Bragg21Garrett Clayton and Chrissie Fit22Bradley Steven Perry and Jake Short23Peyton List and Cameron Boyce24Laura Marano and Raini Rodriguez25Leo Howard and Olivia Holt26Tyrel Jackson Williams and Billy Unger27G. Hannelius and Blake Michael28Garrett Clayton and Chrissie Fit29Bradley Steven Perry and Jake Short30Laura Marano and Raini Rodriguez31Leo Howard and Olivia Holt32Peyton List and Cameron Boyce33Tyrel Jackson Williams and Billy Unger34Laura Marano and Raini Rodriguez35Peyton List and Cameron Boyce36G. Hannelius and Blake Michael37Dove Cameron and Joey Bragg38Bradley Steven Perry and Jake Short39Garrett Clayton and Chrissie Fit40Dove Cameron and Joey Bragg