Irish actor Chris O'Dowd was initially announced as the voice of Tigger but for reasons unknown, he was replaced by Jim Cummings, who has voiced the character for over 20 years alongside Winnie the Pooh.

Jim Cummings has played Winnie the Pooh and Tigger in Disney features since 1988 and 1989 (full time since 1999) respectively.

The character designs of Pooh and his friends is meant to be reminiscent of both their animated selves and the real-life stuffed animals that inspired their adventures.

Before his untimely death, composer Jóhann Jóhannsson was set to score this film.

Brad Garrett 's 15th voice role in a Disney movie.

Winnie the Pooh's third live action appearance after Welcome to Pooh Corner (1983) (as people in costumes) and The Book of Pooh (2001) (as puppets).

The film is to release in 2018, the 30th anniversary of The New Adventures of Winnie the Pooh (1988), the 35th anniversary of both Welcome to Pooh Corner (1983) and Winnie the Pooh and a Day for Eeyore (1983), the 50th anniversary of Winnie the Pooh and the Blustery Day (1968), and the 15th anniversary of Piglet's Big Movie (2003).

Brad Garrett had previously voiced Eeyore on some Disney Winnie the Pooh CD-ROMs which were released in the mid 1990s.

Not to confused with Goodbye Christopher Robin (2017) that recounts the inception of Winnie the Pooh and the Hundred Acre Wood. This film is an entirely fictional story.

Dustin Hoffman, Alan Tudyk, and Martin Short were considered for the voice of Tigger.

This is the second live-action Disney film for Hayley Atwell after Cinderella (2015), Toby Jones after Muppets Most Wanted (2014) and for Ewan McGregor after Beauty and the Beast (2017).

Gemma Arterton was considered to play Christopher Robin's wife Evelyn. However she later decided to not take on the role.

Jim Cummings and Brad Garrett's second Disney film after An Extremely Goofy Movie (2000).

Jim Cummings, Brad Garrett and Wyatt Dean Hall are the only American actors in the film, while the rest of the cast members are from the UK.

Like in A.A. Milne's original stories, this film takes place in a more England setting rather than North America. The designs of some of the animal characters compared to their fully animated counterparts now even reflect their appearances from A.A. Milne's stories (e.g. Tigger's fur is yellow instead of orange, and Piglet's sweater is dark green instead of dark pink).

Wyatt Dean Hall is reprising his role as Roo from Winnie the Pooh (2011).

Peter Capaldi, Toby Jones, Sophie Okonedo, and Mark Gatiss's second time working together since Doctor Who (2005).

The plot of Christopher Robin being an adult was reused from The New Adventures of Winnie the Pooh (1988) series called The New Adventures of Winnie the Pooh: Grown, But Not Forgotten (1991).

This is the first Winnie the Pooh film to be rated PG by the MPAA, rather than G like the previous and fully animated films in the franchise had been.

Young Christopher Robin's outfit is based on the one he wore in the original Ernest Shepard illustrations.

Toby Jones and Mark Gatiss's second time working together since Sherlock (2010).

This is the first Winnie the Pooh film to be shot in the 2.35:1 aspect ratio.

Richard M. Sherman has been confirmed to write three original songs for the film after having done so with his late brother Robert B. Sherman in many of the preceding Disney's Winnie the Pooh feature films, including The Many Adventures of Winnie the Pooh (1977), The Tigger Movie (2000), and also most of the theatrical shorts and one direct-to-video Winnie the Pooh: Seasons of Giving (1999).

The seven year gap between Winnie the Pooh (2011) and Christopher Robin (2018) is the same amount of time between the appearance Owl and Christopher Robin's appearances in the series, after they were completely absent between 2004 and 2011.

This is Brad Garrett's seventh time voicing a character in a live action film, after Teenage Mutant Ninja Turtles: Out of the Shadows (2016) (Krang), The Country Bears (2002) (Fred) Underdog (2007) (Riff Raf), the Night at the Museum trilogy (Easter Island Head), Garfield (2004) (Luca), and Casper (1995) (Fatso).

This is Peter Capaldi's third movie role that features a bear character after playing Mr. Curry in both Paddington (2014) and Paddington 2 (2017).

Prior to the full casting confirmation, Kristen Anderson-Lopez was thought to've been reprising her role as Kanga, after having previously done so in Winnie the Pooh (2011).

Ewan McGregor and Marc Forster's second film project together after Stay (2005).

Toby Jones and Marc Forster's second film together after Finding Neverland (2004).

Jim Cummings is the only cast member from the animated series to be reprising his roles as Pooh and Tigger, whilst the others have different voices from the rest of the series.