| Year | Video | Album | Director |
| 1995 | "Si Tú Te Vas" | Enrique Iglesias | Jon Small[86] |
| 1996 | "Experiencia Religiosa" |
| "Trapecista" |
| 1997 | "Enamorado Por Primera Vez" | Vivir | Jane Simpson[87] |
| "Sólo En Ti" | Fernan Martínez[88] |
"Mystical Experience" (Cameo appearance, with Boyzone) | A Different Beat (US version) | - |
| 1998 | "Esperanza" | Cosas Del Amor | Jaume Collet-Serra[89] |
| 1999 | "Nunca Te Olvidaré" | Julián Pastor[90] |
| "Ruleta Rusa" | J.C. Barros[91] |
"Wild Wild West" (Cameo appearance, with Will Smith) | Wild Wild West Soundtrack | Paul Hunter[91] |
"Bailamos" (Original version) | Cosas Del Amor | Christophe Gstalder |
"Bailamos" (Wild Wild West version) | Nigel Dick[92] |
"Bailamos" (3rd version) | Paul Hunter |
| "Rhythm Divine" / "Ritmo Total" | Enrique | Francis Lawrence[93] |
| 2000 | "Be with You" / "Sólo Me Importas Tú" | Dave Meyers[94] |
"Could I Have This Kiss Forever" (with Whitney Houston) | Francis Lawrence[95] |
| "Sad Eyes" / "Más Es Amar" | David LaChapelle[94] |
"You're My #1" (featuring Sandy & Junior) | - |
"You're My #1" (featuring Valen Hsu) |
"You're My #1" (featuring Alsou) |
| 2001 | "Hero" / "Héroe" | Escape | Joseph Kahn[94] |
| 2002 | "Escape" | Dave Meyers[94] |
"Don't Turn Off the Lights" (1st version and 2nd version) | Marc Klasfeld[96] |
"Love to See You Cry" (Original version, French version and Remix version) | Matthew Rolston[97] |
| "Maybe" | Simon Brand[98][99] |
| "Mentiroso" | Quizás |
| "Quizás" |
| 2003 | "Para Qué la Vida" |
"To Love a Woman" (with Lionel Richie) | Escape |
"Addicted" (US version and UK version) | 7 | Peter Berg[100] |
| "Adicto" |
| 2004 | "Not in Love" (featuring Kelis) | Jake Nava[101] |
| 2007 | "Do You Know? (The Ping Pong Song)" / "Dímelo" | Insomniac | Jessy Terrero[94] |
| "Somebody's Me" / "Alguien Soy Yo" | Anthony Mandler[94] |
| "Tired of Being Sorry" | Jessy Terrero[102] |
| 2008 | "Push" (featuring Lil Wayne / Prophet) | Billy Woodruff[94] |
| "Can You Hear Me" | Greatest Hits | Paul Minor[103][104][105] |
"Tired of Being Sorry (Laisse Le Destin L'emporter)" (featuring Nâdiya) | Électron Libre | - |
"Away" (featuring Sean Garrett) | Greatest Hits | Anthony Mandler[106] |
| "¿Dónde Están Corazón?" | 95/08 Éxitos | Paul Minor[103] |
"Lloro Por Ti" (Original version and Remix version featuring Wisin & Yandel) |
| 2009 | "Takin' Back My Love" (featuring Ciara / Sarah Connor) | Greatest Hits | Ray Kay[107] |
"Gracias a Ti" (Remix, with Wisin & Yandel) | La Revolución: Evolution | Jessy Terrero[108] |
| 2010 | "Cuando Me Enamoro" (featuring Juan Luis Guerra) | Euphoria |
"I Like It" (featuring Pitbull) | Wayne Isham[94] |
"I Like It" (Jersey Shore version, featuring Pitbull) | David Rousseau[109] |
"Heartbeat" (Original version featuring Nicole Scherzinger and 'India Mix' version featuring Sunidhi Chauhan) | Hiro Murai[110] |
"No Me Digas Que No" (Original version featuring Wisin & Yandel and solo version) | Jessy Terrero[111] |
"Tonight I'm F**kin' You" (Lyric video, featuring Ludacris and DJ Frank E) | - |
"Tonight I'm F**kin' You" / "Tonight I'm Lovin' You" (featuring Ludacris and DJ Frank E) | BBGun & Parris[112] |
| 2011 | "Dirty Dancer" (featuring Usher and Lil Wayne) | Yasha Malekzad, Jeff Dotson and Ethan Lader |
| "Ayer" | Evan Winter[113] |
"I Like How It Feels" (featuring Pitbull & The WAV.s) | Sex and Love | Enrique Iglesias |
"Naked" (with Dev) | The Night the Sun Came Up | BBGun |
| 2012 | "Finally Found You" (Lyric video, featuring Sammy Adams) | Sex and Love | - |
"Tchu Tchu Tcha" (The Global Warming Listening Party video, with Pitbull) | Global Warming | Don Tyler[114] |
"Finally Found You" (featuring Sammy Adams / Daddy Yankee) | Sex and Love | Diego Hurtado de Mendoza[115] |
| 2013 | "Turn the Night Up" (Fan version) | Lior Molho[116] |
| "Turn the Night Up" | Yasha Malekzad |
"Loco" (featuring Romeo Santos) |
"Heart Attack" (Lyric video) | - |
| "Heart Attack" | Colin Tilley |
| 2014 | "El Perdedor" (Original version and Bachata version, featuring Marco Antonio Solís) | Jessy Terrero |
"I'm a Freak" (featuring Pitbull) | Colin Tilley |
"I'm a Freak" (Lyric video, featuring Pitbull) | - |
"Bailando" (featuring Descemer Bueno and Gente de Zona) | Alejandro Pérez |
"Bailando" (English version, featuring Sean Paul, Descemer Bueno and Gente de Zona) |
"Bailando" (Brazilian version, featuring Luan Santana, Descemer Bueno and Gente de Zona) |
"Bailando" (Portuguese version, featuring Mickael Carreira, Descemer Bueno and Gente de Zona) |
"Bailando" (Portuguese version lyric video, featuring Luan Santana) | - |
"Bailando" (Brazilian version lyric video, featuring Mickael Carreira) |
| 2015 |
"Let Me Be Your Lover" (featuring Pitbull) |
Alejandro Pérez[117][118] |
"Noche y Dia" (released as "Noche y de Dia", featuring Yandel and Juan Magan) |
"El Perdón/Forgiveness" (with Nicky Jam) | | Jonathan Craven and Darren Craig |
| 2016 | "Messin' Around" (with Pitbull) | Climate Change | David Rousseau |
"Duele El Corazon" (featuring Wisin) | | Alejandro Pérez |
| 2017 | "Súbeme La Radio" (featuring Descemer Bueno and Zion & Lennox) | |
| 2018 | "El Baño" (featuring Bad Bunny) | | Enrique Iglesias and Maxim Bohichik |
"Nos Fuimos Lejos" (with Descemer Bueno featuring El Micha) | | Pedro Vázquez |
"Move to Miami" (featuring Pitbull) | | Fernando Lugo |
| 2019 | "Después Que Te Perdí" (with Jon Z) | | Alejandro Pérez |
| 2023 | "Así Es La Vida" (with María Becerra) | | Maxim Bohichik |