In the segment "Mickey & Minnie's Gift of the Magi", the Dixieland jazz band at the charity toy drive is made up of firefighters and named the Firehouse 5. This is a nod to the Firehouse Five Plus Two, a seven-piece Dixieland jazz band founded in 1949 and consisting of Disney animation staff (including lead animators Ward Kimball and Frank Thomas, two of Disney's famed Nine Old Men).

In the "A Very Goofy Christmas" segment, there are lawn flamingos dressed up for the holidays. They are based on the flamingos from "The Carnival of the Animals" segment in Fantasia 2000 (1999), which was in production at the same time as "Mickey's Once Upon a Christmas".

In the segment "A Very Goofy Christmas", one of the ornaments Goofy puts on the tree is Angelique, from Beauty and the Beast: The Enchanted Christmas (1997).

The department store Minnie works at, in the segment "Mickey & Minnie's Gift of the Magi", is named "Mortimer's". Mortimer is the name Walt Disney originally intended to give to Mickey Mouse. (Minnie's boss at the department store is Mortimer Mouse, a character who first appeared in the cartoon Mickey's Rival (1936).)

Jim Cummings voices six different characters in this movie.

The scene in the mall, during the "A Very Goofy Christmas" segment, parodies several "Indiana Jones" escape sequences.

Mortimer is voiced in this movie by Jeff Bennett. In his later appearances, Mortimer is voiced by Maurice LaMarche.

Jim Cummings (the voice of Pete) and Mae Whitman (the voice of the little girl) would later star in The Jungle Book 2 (2003) as the voices of Kaa and Colonel Hathi, and Shanti, respectively.

The snowboard Max asks for is a twin tip, but the board he received is a directional single tip.

Despite this movie being 3 different stories created together, this is the first time that the entirety of Disney's classic sensational six appear in their very own full-length animated feature.

Mickey's dance during the Gift of the Magi segment is redrawn animation from Mickey's Birthday Party (1942).

Kelsey Grammer, Tress Macneille and Russi Talyor also co-starred in "The Simpsons" as recurring characters.

This is the last non-theatrically released Disney movie of the 20th century.