Ewan McGregor as Christopher Robin

Hayley Atwell as Evelyn Robin

Kumud Pant as Train Passenger

Bronte Carmichael as Madeline Robin

Jim Cummings as Winnie the Pooh / Tigger (voice)

Brad Garrett as Eeyore (voice)

Nick Mohammed as Piglet (voice)

Toby Jones as Owl (voice)

Peter Capaldi as Rabbit (voice)

Sophie Okonedo as Kanga (voice)

Sara Sheen as Roo (voice)

Mark Gatiss as Giles Winslow

Oliver Ford Davies as Old Man Winslow

Ronkẹ Adékoluẹjo as Katherine Dane

Adrian Scarborough as Hal Gallsworthy

Roger Ashton-Griffiths as Ralph Butterworth

Ken Nwosu as Paul Hastings

Amanda Lawrence as Joan MacMillan

John Dagleish as Matthew Leadbetter

Orton O'Brien as Young Christopher Robin

Katy Carmichael as Christopher Robin's Mother

Tristan Sturrock as Christopher Robin's Father

Jasmine-Simone Charles as Little Girl

Paul Chahidi as Cecil Hungerford

Matt Gavan as Snooty Businessman

Gareth Mason as Balloon Vendor

Summer Brooks as Balloon Holder

Amrou Al-Kadhi as Nemir Azizi

Zain Falzon as Boy in Stroller

Rainy Milo as Boy's Mother

Michael Jenn as London Train Conductor

Souad Faress as Wealthy Woman

Alan Clark as Sussex Train Attendant

Chris Pratt as Sussex Train Porter

Harriet Leitch as Tea Server

Vera Chok as Margaret King (Train Passenger #1)

Claire Redcliffe as Boarding School Teacher

Elsa Minell Solak as Madeline 3 Years Old

Matt Berry as Policeman Bobby

Simon Farnaby as Taxi Driver

Matthew Earley as Truck Driver

Mackenzie Crook as Newspaper Seller

Vivien Bridson as Old Man Winslow's Secretary

Narinder Samra as Milkman

Oliver Payne as Milk Delivery Boy

David Hartley as Man on Bus

Clara McGregor as Girl in Aircraft Design Office

Raj Ghatak as Neel Chawla (Barrel Mover)

Abbey Denne as Girlfriend (uncredited)

Gintare Beinoraviciute as Passerby (uncredited)

Roy Beck as Winslow Board Director (uncredited)

Shola Adewusi as Rosemary Hopwood (uncredited)

Tim Ingall as Jimmy Knowait (uncredited)