Ewan McGregor as Christopher Robin

Hayley Atwell as Evelyn Robin

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

Ronkẹ Adékoluẹjo as Katherine Dane

Adrian Scarborough as Hal Gallsworthy

Roger Ashton-Griffiths as Ralph Butterworth

Ken Nwosu as Paul Hastings

John Dagleish as Matthew Leadbetter

Amanda Lawrence as Joan MacMillan

Tristan Sturrock as Alan Alexander Milne

Katy Carmichael as Daphne de Sélincourt

Paul Chahidi as Cecil Hungerford

Orton O'Brien as Christopher Robin (Young)

Elsa Minell Solak as Madeline Robin (Kid)

Amrou Al-Kadhi as Nemir Azizi

Vera Chok as Margaret King

Raj Ghatak as Neel Chawla

Oliver Ford Davies as Old Man Winslow

Vivien Bridson as Old Man Winslow's Secretary

Matt Berry as Policeman Bobby

Jasmine-Simone Charles as Little Girl

Harriet Leitch as Tea Server

Souad Faress as Wealthy Woman

Claire Redcliffe as Boarding School Teacher

Matt Gavan as Snooty Businessman

Mackenzie Crook as Newspaper Seller

Clara McGregor as Girl in Aircraft Design Office

Gareth Mason as Balloon Vendor

Summer Brooks as Balloon Holder

Zain Falzon as Boy in Stroller

Rainy Milo as Boy's Mother

Simon Farnaby as Taxi Driver

Matthew Earley as Truck Driver

Narinder Samra as Milkman

Oliver Payne as Milk Delivery Boy

Kumud Pant as Train Passenger

Michael Jenn as London Train Conductor

Alan Clark as Sussex Train Attendant

Chris Pratt as Sussex Train Porter

Shola Adewusi as Rosemary Hopwood

Tim Ingall as Jimmy Knowait

Peter Singh as Ravi Patel

Connor Haywood as Lance Corporal

Jackson Kai as Cricketer

Richard M. Sherman as Singer

Olga Docheva as Book Store Customer

David Evestaff as WWII Soldier

Stuart Cooke as Billboard Worker

Mary Yeomans as Tradesman

A.k. Steppa as Platform Shop Vendor

Matt Harvey as Head Boy

Ethan Keaton as Homeless Man

Thomas Padden as Businessman

Roy Beck as Winslow Board Director

Caroline Garnell as Winslow Efficiency Room Worker

Richard Price as Winslow Office Worker

Chloe Swan Sparwath as Winslow Junior Office Worker

Rupert Turnbull as Red-Haired Boy

Kai Scarlett Williams as Market Boy

Evie Wray as Market Boy's Mother

Lee Asquith-Coe as School Porter

Nick Davison as Station Porter

Rutvig Vaid as Station Porter

Niamh O'Mahony as Woman on Bus

Gino Picciano as Man on the Bus

David Hartley as Man on the Bus

Errol Francis as Railway Passenger

Bern Collaço as Train Passenger

Dean Middhat as Train Passenger

Marco Mastrocola as Train Passenger

Gary Thompsett as Train Passenger

Jeremy Oliver as Commuter

Sharron Spice as Commuter

Anthony Richard Rowe as Home Guard

Mark Sayers as Home Guard

John Whitby as Passerby

Karol Steele as Passerby

Karen Smyth as Passerby

Christopher Haley as Passerby

Chloe-Megan Child as Passerby

Gintare Beinoraviciute as Passerby