As promised.
Chronology: 1400s, the Atlantic century
1425-29 --- Fernando de Castro’s and Diego de Silves’ expeditions in West Africa funded by King Joao I and his son Prince Enrique
1433-38 --- During King Duarte's five years reign, Gil Eannes reaches Fernando Po
1438 --- King Duarte dies, starts the troubled regency of Pedro Duke of Coimbra upon Afonso V
1446 --- Alvaro Fernandez reaches the coasts of an unknown continent South-West of Cape Verde archipelago
1446-51 --- In King Afonso V's early adulthood, 2nd Moroccan War begins. Portugal conquers Tangiers
1452-53 --- War with Castile against Aragon
1453 --- Dakar is capital of the newly-established Portuguese West Africa
1455 --- Alvise Ca' da Mosto reaches and circumnavigate Cape of Good Hope
1458-59 --- Another conflict with Castile against Aragon, Afonso V captures Barcelona and receives a tribute
1462 --- Portuguese Austral Africa is established (Sao Borge in Karroo is first settlement), in the same year the first trading post is settled in Brazil
1473 --- Brazil, the third Portuguese overseas dominion, is established
1481-95 --- The warring reign of Joao II: in 14 years Portugal fights against Granada, North African Sultanates, England, Spain and Indian nations
1489 --- Tangiers is lost to Morocco in a disgraceful peace treaty
1490-92 --- Wars does not halt Portuguese explorations: Cristovao Colombo uncovers Caribbean Sea and North Atlantic, Bartolomeu Diaz reaches India, Pedro da Covilha makes contact with Inca Empire
1495 --- Manuel I succeeds his cousin Joao II
1497 --- Braga reaches Cape Horn
1497-98 --- During the Iberian War, the Spaniards under the Old Duke of Alba temporary take Porto and besiege Lisbon
1498 --- The Portuguese capture Mombasa and temporary subjugate the Sultanate of Kilwa, Altamira's guides an expedition in the interior of Eastern Africa
1499 --- On the way of his imaginary "North-West passage" to Asia Cristovao Colombo reaches Greenland and Hudson Bay
[Author]: When the connection with my pic-host resumes, I'll post some screenies about the situation of the known world as of 1st January 1500