Nick MohammedPiglet (voice)
Toby JonesOwl (voice)
Sara SheenRoo (voice)
Ronkẹ AdékoluẹjoKatherine Dane
Roger Ashton-GriffithsRalph Butterworth
Ken NwosuPaul Hastings
John DagleishMatthew Leadbetter
Amanda LawrenceJoan MacMillan
Tristan SturrockAlan Alexander Milne
Katy CarmichaelDaphne de Sélincourt
Paul ChahidiCecil Hungerford
Orton O'BrienChristopher Robin (Young)
Elsa Minell SolakMadeline Robin (Kid)
Amrou Al-KadhiNemir Azizi
Vera ChokMargaret King
Raj GhatakNeel Chawla
Oliver Ford DaviesOld Man Winslow
Vivien BridsonOld Man Winslow's Secretary
Matt BerryPoliceman Bobby
Jasmine-Simone CharlesLittle Girl
Harriet LeitchTea Server
Souad FaressWealthy Woman
Claire RedcliffeBoarding School Teacher
Matt GavanSnooty Businessman
Mackenzie CrookNewspaper Seller
Clara McGregorGirl in Aircraft Design Office
Gareth MasonBalloon Vendor
Summer BrooksBalloon Holder
Zain FalzonBoy in Stroller
Rainy MiloBoy's Mother
Simon FarnabyTaxi Driver
Matthew EarleyTruck Driver
Narinder SamraMilkman
Oliver PayneMilk Delivery Boy
Kumud PantTrain Passenger
Michael JennLondon Train Conductor
Alan ClarkSussex Train Attendant
Chris PrattSussex Train Porter
Shola AdewusiRosemary Hopwood
Tim IngallJimmy Knowait
Peter SinghRavi Patel
Connor HaywoodLance Corporal
Jackson KaiCricketer
Richard M. ShermanSinger
Olga DochevaBook Store Customer
David EvestaffWWII Soldier
Mary YeomansTradesman
A.k. SteppaPlatform Shop Vendor
Matt HarveyHead Boy
Ethan KeatonHomeless Man
Thomas PaddenBusinessman
Roy BeckWinslow Board Director
Caroline GarnellWinslow Efficiency Room Worker
Richard PriceWinslow Office Worker
Chloe Swan SparwathWinslow Junior Office Worker
Rupert TurnbullRed-Haired Boy
Kai Scarlett WilliamsMarket Boy
Evie WrayMarket Boy's Mother
Lee Asquith-CoeSchool Porter
Nick DavisonStation Porter
Rutvig VaidStation Porter
Niamh O'MahonyWoman on Bus
Gino PiccianoMan on the Bus
David HartleyMan on the Bus
Errol FrancisRailway Passenger
Bern CollaçoTrain Passenger
Dean MiddhatTrain Passenger
Marco MastrocolaTrain Passenger
Gary ThompsettTrain Passenger
Jeremy OliverCommuter
Sharron SpiceCommuter
Anthony Richard RoweHome Guard
Mark SayersHome Guard
John WhitbyPasserby
Karol SteelePasserby
Karen SmythPasserby
Christopher HaleyPasserby
Chloe-Megan ChildPasserby
Gintare BeinoraviciutePasserby
