Sleepy Hollow (1999)

On the Town (1949)
Ichabod introduces his adopted son to New York City by saying, "You'll soon find your bearings, young Masbeth. The Bronx is up, the Battery is down, and home is this way."

Horror of Dracula (1958)

The Hound of the Baskervilles (1959)

The Brides of Dracula (1960)
The windmill scene is closely copied.

Black Sunday (1960)

Pit and the Pendulum (1961)

Kill Baby, Kill (1966)

Faerie Tale Theatre: Aladdin and His Wonderful Lamp (1986) (TV Episode)
In Treasure Cave we can see the same images of monsters as on lantern in the 1999 film "Sleepy Hollow"

Evil Dead II (1987)

Batman (1989)

The Silence of the Lambs (1991)

Army of Darkness (1992)

The Nightmare Before Christmas (1993)

Dead Man (1995)

Referenced in

The Critic: Episode #1.6 (TV Episode)
Jay admits that he liked the film

Movie Stars: The Two Faces of Steve (2000) (TV Episode)
"[Playing the] beheaded blacksmith in Sleepy Hallow won't land me on the cover of Vanity Fair."

Brotherhood of the Wolf (2001)

Cradle of Fear (2001) (Video)
on magazine cover

Jeepers Creepers (2001)

You Shoot, I Shoot (2001)
A poster of the film is shown hanging on a wall.

Don't Say a Word (2001)

Eternal Blood (2002)

Overnight (2003)
Boondock Saints is shown to be playing in a double feature with Sleepy Hollow

Charlie and the Chocolate Factory (2005)
The bizarre glasses that Wonka wears upon first meeting the children reference similar ones seen in Burton/Depp's Sleepy Hollow.

Corpse Bride (2005)
In the beginning of both films Johnny Depp's characters frees a flying animal (bird and butterfly) from its cage and lets it fly out of his window.

Assume the Position with Mr. Wuhl (2006) (TV Movie)
Wuhl mentions Johnny Depp's movie

Top Gear: Episode #8.5 (2006) (TV Episode)
Gambon mentions he's in it

Wicked Little Things (2006)
daughter says that the woods remind her of that Johnny Depp movie where the guy gets his head cut off, then she mentions the "legend of Sleepy Hollow"

The Tracey Fragments (2007)
movie on shelf in store

Be Kind Rewind (2008)
DVD case is shown.

Troldspejlet: Episode #39.5 (2008) (TV Episode)
Jakob Stegelman mentions the film in his review of Sweeney Todd: The Demon Barber of Fleet Street (2007)

Bum Reviews: Red Riding Hood (2011) (TV Episode)
Plots are compared

Midnight Movie Review: Sleepy Hollow (2011) (TV Episode)
the number 6 in the Top 25 Best '90s Horror Movies.

Geek Charming (2011) (TV Movie)
The film school geeks mention the title at the film festival

Face Off: Burtonesque (2012) (TV Episode)
title mentioned

Jeopardy!: Episode #28.181 (2012) (TV Episode)
referenced in clue in "A Johnny Depp Film Fest" category

Featured in

Sleepy Hollow: Behind the Legend (2000) (Video)

Troldspejlet: Episode #23.10 (2000) (TV Episode)
reviewed + footage used

The 72nd Annual Academy Awards (2000) (TV Special)

Bobby (2002)
Clips from the movie play in the background during the second song.

The Cutting Edge: The Magic of Movie Editing (2004)
Clip included; editing analysed.

A Trip to Sleepy Hollow (2009) (Short)
Clips of this movie were shown.

The Rotten Tomatoes Show: Cop Out/The Crazies/A Prophet (2010) (TV Episode)
"Tim Burton in 3 Minutes or Less" segment.

Hewy's Animated Movie Reviews: The Top 13 Scariest Animated Monsters (2011) (TV Episode)
Hewy discusses Tim Burton's version of the Headless Horseman

The Nostalgia Chick: Sleepy Hollow (2012) (TV Episode)
movie is reviewed

Spoofed in

Jay and Silent Bob Strike Back (2001)

Stockflame (2005) (Short)
The Rodenstein Knight was a Hessian mercenary with the love of carnage too. He was also cursed and forced to return after his death. He is a well-versed sword-fighter.