| Jan van Calcar | Habsburg Netherlands | 1499–1546 | 5 |
| Yi Am | — | 1499 | 1 |
| Hans Asper | Switzerland | 1499–1571 | 1 |
| Wen Jia | Ming dynasty | 1499–1582 | 1 |
| Friedrich Hagenauer | Germany | 1499–1546 | 29 |
| Pâris Bordone | Republic of Venice | 1500–1571 | 37 |
| Jan Sanders van Hemessen | Habsburg Netherlands | 1500–1575 | 22 |
| Maître des études de draperies | Germany | 1500 | 8 |
| Maître de Saint Gilles | France | 1500–1600 | 6 |
| Benvenuto Cellini | Republic of Florence | 1500–1571 | 4 |
| Pedro García de Benavarre | Kingdom of Aragon | 1500–1500 | 6 |
| Maître de Paul et Barnabé | — | 1500–1599 | 1 |
| Maître de la Légende de sainte Godelieve | — | 1500 | 1 |
| Frei Carlos | Reino de Portugal | 1500–1600 | 1 |
| Adriaen Isenbrant | Habsburg Netherlands | 1500–1551 | 22 |
| Cornelis Bazelaere | Habsburg Netherlands | 1500–1530 | 5 |
| Pere Espalargues | Kingdom of Aragon | 1500–1550 | 1 |
| Juan de Borgoña le jeune | Spain | 1500–1565 | 1 |
| Jan Cornelisz Vermeyen | Habsburg Netherlands | 1500–1559 | 12 |
| Brugse Meester van de Heilige Ildefonsus | — | 1500 | 2 |
| Maître de la Manne | — | 1500–1500 | 1 |
| Marco Marziale | Republic of Venice | 1500–1600 | 5 |
| Josse Lieferinxe | France | 1500–1508 | 9 |
| Maestro di Tavarnelle | — | 1500–1600 | 1 |
| Maître de Dreux Budé | — | 1500–1450 | 1 |
| Hans Sebald Beham | Germany | 1500–1550 | 234 |
| Girolamo Mazzola Bedoli | — | 1500–1569 | 5 |
| Maître de Saint-Séverin | Germany | 1500–1600 | 3 |
| Maître de 1518 | — | 1500–1530 | 7 |
| Maître de l'Adoration von Groote | — | 1500–1520 | 11 |
| Maître de Griselda | Republic of Siena | 1500 | 4 |
| Meester van Pratovecchio | — | 1500–1500 | 11 |
| Meister des Mornauer-Portraits | Germany | 1500 | 3 |
| Maître de la Vie de Marie | Germany | 1500–1500 | 10 |
| Maître de Marradi | — | 1500–1600 | 8 |
| Maître de l'Autel d'Aix-la-Chapelle | Germany | 1500–1600 | 5 |
| Callisto Piazza | — | 1500–1561 | 5 |
| Maître des Portraits Baroncelli | County of Flanders | 1500–1600 | 3 |
| Maître des Portraits princiers | Southern Netherlands | 1500 | 2 |
| Maître de Meßkirch | Holy Roman Empire | 1500–1543 | 15 |
| Pietro di Niccolò Duia | — | 1500–1600 | 1 |
| Meister des Sebastians-Diptychons | Germany | 1500–1600 | 1 |
| Meister von Sigmaringen | Germany | 1500–1600 | 1 |
| Maître des portraits Brandon | Southern Netherlands | 1500 | 1 |
| Guglielmo Della Porta | Italy | 1500–1577 | 2 |
| Maître du Retable de Heisterbach | — | 1500–1500 | 3 |
| Maître de la Passion de Lyversberg | Germany | 1500–1500 | 2 |
| Jan Mandyn | Habsburg Netherlands | 1500–1560 | 2 |
| Alunno di Benozzo | — | 1500 | 1 |
| Maître de l'Adoration d'Anvers | Southern Netherlands | 1500–1600 | 4 |
| Matthias Gerung | Germany | 1500–1570 | 1 |
| Giovanni Francesco Bezzi | — | 1500–1571 | 1 |
| Wolfgang Beurer | — | 1500 | 2 |
| Maître de la Madone André | — | 1500–1600 | 1 |
| Bonanat Zaortiga | Spain | 1500–1500 | 5 |
| Andrés de Melgar | Spain | 1500–1554 | 2 |
| Pere Gascó | Spain | 1500–1546 | 1 |
| Master of Badalona | — | 1500–1500 | 1 |
| Francesco Binasco | — | 1500 | 1 |
| Domenico Campagnola | Republic of Venice | 1500–1564 | 21 |