| Jan van Calcar | Habsburg Netherlands | 1499–1546 | 5 |
| Yi Ahm | — | 1499 | 1 |
| Hans Asper | Switzerland | 1499–1571 | 1 |
| Wen Jia | Ming dynasty | 1499–1582 | 1 |
| Friedrich Hagenauer | Germany | 1499–1546 | 29 |
| Paris Bordone | Republic of Venice | 1500–1571 | 37 |
| Jan Sanders van Hemessen | Habsburg Netherlands | 1500–1575 | 22 |
| Master of the Drapery Studies | Germany | 1500 | 8 |
| Master of Saint Giles | France | 1500–1600 | 6 |
| Benvenuto Cellini | Republic of Florence | 1500–1571 | 4 |
| Pedro García de Benavarre | Kingdom of Aragon | 1500–1500 | 6 |
| Master of Paulus and Barnabas | — | 1500–1599 | 1 |
| Master of the Saint Godelieve Legend | — | 1500 | 1 |
| Frei Carlos | Reino de Portugal | 1500–1600 | 1 |
| Adriaen Isenbrandt | Habsburg Netherlands | 1500–1551 | 22 |
| Master with the Parrot | Habsburg Netherlands | 1500–1530 | 5 |
| Pere Espallargues | Kingdom of Aragon | 1500–1550 | 1 |
| Juan de Borgoña the Younger | Spain | 1500–1565 | 1 |
| Jan Cornelisz Vermeyen | Habsburg Netherlands | 1500–1559 | 12 |
| Master of the Pacully collection | — | 1500 | 2 |
| Master of the Gathering of the Manna | — | 1500–1500 | 1 |
| Marco Marziale | Republic of Venice | 1500–1600 | 5 |
| Josse Lieferinxe | France | 1500–1508 | 9 |
| Master of Tavarnelle | — | 1500–1600 | 1 |
| Master of Dreux Budé | — | 1500–1450 | 1 |
| Hans Sebald Beham | Germany | 1500–1550 | 234 |
| Girolamo Mazzola Bedoli | — | 1500–1569 | 5 |
| Master of Saint Severin | Germany | 1500–1600 | 3 |
| Master of 1518 | — | 1500–1530 | 7 |
| Master of the Von Groote Adoration | — | 1500–1520 | 11 |
| Master of the Griselda Legend | Republic of Siena | 1500 | 4 |
| Master of Pratovecchio | — | 1500–1500 | 11 |
| Master of the Mornauer Portrait | Germany | 1500 | 3 |
| Master of the Life of the Virgin | Germany | 1500–1500 | 10 |
| Master of Marradi | — | 1500–1600 | 8 |
| Master of the Aachen Altar | Germany | 1500–1600 | 5 |
| Callisto Piazza | — | 1500–1561 | 5 |
| Master of the Baroncelli Portraits | County of Flanders | 1500–1600 | 3 |
| Master of Portraits of Princes | Southern Netherlands | 1500 | 2 |
| Master of Messkirch | Holy Roman Empire | 1500–1543 | 15 |
| Pietro di Niccolò Duia | — | 1500–1600 | 1 |
| Master of the Sebastian Diptych | Germany | 1500–1600 | 1 |
| Meister von Sigmaringen | Germany | 1500–1600 | 1 |
| Master of the Brandon Portrait | Southern Netherlands | 1500 | 1 |
| Guglielmo della Porta | Italy | 1500–1577 | 2 |
| Master of the Heisterbach Altar | — | 1500–1500 | 3 |
| Master of the Lyversberger Passion | Germany | 1500–1500 | 2 |
| Jan Mandijn | Habsburg Netherlands | 1500–1560 | 2 |
| Alunno di Benozzo | — | 1500 | 1 |
| Master of the Antwerp Adoration | Southern Netherlands | 1500–1600 | 4 |
| Matthias Gerung | Germany | 1500–1570 | 1 |
| Nosadella | — | 1500–1571 | 1 |
| Wolfgang Beurer | — | 1500 | 2 |
| Master of the André Virgin | — | 1500–1600 | 1 |
| Bonanat Zaortiga the Elder | 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 |