| Untitled illustration | 1999 | Lorenzo Pastrovicchio | Illustration | 2 | Italy | 211 |
| All Of Me | 1999 | Stefan Petrucha, Cèsar Ferioli Pelaez | Story | 36 | Denmark | 35 |
| Buonanotte | 1999 | Alessandro Perina | Story | 1 | Italy | 27 |
| 6 Σπέσιαλ τεύχη | 1999 | | Illustration | 1 | Non-Disney and/or non-comics | 25 |
| Chance Encounters | 1999 | Sarah Kinney, Francisco Rodriguez Peinado | Story | 10 | Denmark | 22 |
| Pals | 1999 | Dave Rawson, Francisco Rodriguez Peinado | Story | 9 | Denmark | 21 |
| We droomden dat... we in een huifkar woonden! | 1999 | Wilma van den Bosch | Centrefold or poster | 2 | Holland | 21 |
| We droomden dat... we alles durfden! | 1999 | Wilma van den Bosch | Centrefold or poster | 2 | Holland | 21 |
| Flea Circus | 1999 | Sarah Kinney, Jorge David Redo | Story | 9 | Denmark | 20 |
| We droomden dat... we politieagenten waren! | 1999 | Wilma van den Bosch | Centrefold or poster | 2 | Holland | 20 |
| We droomden dat... we bij de brandweer waren! | 1999 | Wilma van den Bosch | Centrefold or poster | 2 | Holland | 19 |
| That Milk Chocolate Touch | 1999 | Stefan Petrucha, Jorge David Redo | Story | 3 | Denmark | 18 |
| We droomden dat... we op de noordpool woonden! | 1999 | Wilma van den Bosch | Centrefold or poster | 2 | Holland | 15 |
| Minni e lo spirito dell'artista | 1999 | Nino Russo, Alessia Martusciello | Story | 24 | Italy | 15 |
| The Town That Hated Mickey | 1999 | Michael T. Gilbert, Joaquín Cañizares Sanchez | Story | 35 | Denmark | 14 |
| We droomden dat... ons huis van snoep was! | 1999 | Wilma van den Bosch | Centrefold or poster | 2 | Holland | 13 |
| Le pantofole | 1999 | Alessandro Perina | Story | 1 | Italy | 12 |
| Kerstcollecte Boris | 1999 | Frank Jonker, Comicup Studio | Story | 5 | Holland | 11 |
| How To Make Comics | 1999 | Stefan Printz-Påhlson, Cèsar Ferioli Pelaez | Story | 2 | Denmark | 10 |
| A tavola | 1999 | Alessandro Perina | Story | 1 | Italy | 10 |
| Pluto viaggiatore da guardia | 1999 | Carlo Panaro, Marco Forcelloni | Story | 20 | Italy | 10 |
| Tanti auguri, Gancio! | 1999 | Luca Boschi, Alessandro Perina | Story | 30 | Italy | 10 |
| Eta Beta e gli abiti F.A.B. | 1999 | Carlo Panaro, Andrea Maccarini | Story | 26 | Italy | 8 |
| Rock 'n' roll | 1999 | Alessandro Perina | Story | 1 | Italy | 8 |
| The Pet Contest | 1999 | François Corteggiani, José Antonio González | Story | 1 | France | 7 |
| Jeux vidéo | 1999 | | Cover | 1 | France | 7 |
| Legpuzzels | 1999 | Evert Geradts, Santiago Barreira | Story | 4 | Holland | 7 |
| We droomden dat... we konden vliegen! | 1999 | Wilma van den Bosch | Centrefold or poster | 2 | Holland | 7 |
| Minni e Musetta | 1999 | Gisella Rivolo Scott | Story | 15 | Italy | 7 |
| Il Pluto spaziale | 1999 | Nino Russo, Roberto Ronchi | Story | 5 | Italy | 7 |
| Topolino testimone scomodo | 1999 | Marco Bosco, Maurizio Amendola | Story | 18 | Italy | 7 |
| Il boomerang | 1999 | Alessandro Perina | Story | 1 | Italy | 7 |
| Al ristorante | 1999 | Alessandro Perina | Story | 1 | Italy | 7 |
| Untitled cover | 1999 | | Cover | 1 | Italy | 7 |
| Untitled cover | 1999 | Tello-Team | Cover | 1 | Denmark | 6 |
| Untitled cover | 1999 | Gerben Steenks | Cover | 1 | Holland | 6 |
| We droomden dat... we konden goochelen! | 1999 | Wilma van den Bosch | Centrefold or poster | 2 | Holland | 6 |
| Minni e il Pluto bis | 1999 | Nino Russo, Maria Luisa Uggetti | Story | 16 | Italy | 6 |
| Untitled cover | 1999 | Davide Cesarello | Cover | 1 | Italy | 6 |
| Untitled cover | 1999 | Corrado Mastantuono | Cover | 1 | Italy | 6 |
| Untitled cover | 1999 | Francesco Artibani, Corrado Mastantuono | Cover | 1 | Italy | 6 |
| Untitled cover | 1999 | Francesco Artibani, Corrado Mastantuono | Cover | 1 | Italy | 6 |
| Untitled cover | 1999 | Hjemmet Oslo, Tello-Team | Cover | 1 | Denmark | 5 |
| Går de i ring? | 1999 | Tello-Team | Game or puzzle | 1 | Denmark | 5 |
| The Chase | 1999 | François Corteggiani, Maximino Tortajada Aguilar | Story | 1 | France | 5 |
| Untitled story | 1999 | François Corteggiani, Maximino Tortajada Aguilar | Story | 1 | France | 5 |
| Topolino e il dono dell'imperatore | 1999 | Alessandro Sisti, Stefano Mirone | Story | 4 | Italy | 5 |
| Quando Minni è in vacanza | 1999 | Diego Fasano, Luciano Gatto | Story | 28 | Italy | 5 |
| Tip & Tap e lo street bar | 1999 | Diego Fasano, Carlo Limido | Story | 20 | Italy | 5 |
| Untitled cover | 1999 | Stefano Mirone | Cover | 1 | Italy | 5 |
| Untitled cover | 1999 | Stefano Mirone | Cover | 1 | Italy | 5 |
| Hundeshow | 1999 | Tello-Team | Game or puzzle | 1 | Denmark | 4 |
| 漂亮的房子 | 1999 | Tello-Team | Game or puzzle | 1 | Denmark | 4 |
| Geburtstag um Mitternacht! | 1999 | Tello-Team | Game or puzzle | 2 | Denmark | 4 |
| Buchstaben-Labyrinth | 1999 | Studio Bonnet | Game or puzzle | 1 | Denmark | 4 |
| The Imp And I | 1999 | 川出恵三 (Keizō Kawade), Joaquín Cañizares Sanchez | Story | 19 | Denmark | 4 |
| Mickey dans Safari à la une | 1999 | Alain Clément, José Ramón Bernado | Story | 16 | France | 4 |
| Topolino e il Trapper Trophy | 1999 | Alessandro Sisti, Marco Mazzarello | Story | 4 | Italy | 4 |
| Untitled cover | 1999 | | Cover | 1 | Italy | 4 |
| Untitled cover | 1999 | Francesco Artibani, Corrado Mastantuono | Cover | 1 | Italy | 4 |