1500:

Ireland, ca. 1500
Regional map of Ireland and Northern Ireland showing the four provinces and regional clan associations around 1500. Edited by Samuel Rawson Gardiner, published by Longmans, Green, and Co. in 1892, and made available at Ancestry.com. Click the image to see the map in a larger version in a separate window.

1525:

Sengoku Daimyo Circa 1525
Very large, attractive map of Japan by Christopher West at the Samurai Archives site

1543:

Uesugi Unification of Echigo 1543-1551
A clear representation of the various factions of Echigo, Japan, by Christopher West at the Samurai Archives site. 

1545:

Sengoku Daimyo Circa. 1545
Very large, attractive map of Japan by Christopher West at the Samurai Archives site. 

1550:

Sengoku Daimyo Circa 1550
Very large, attractive map of Japan by Christopher West at the Samurai Archives site. 

1550:

Ireland, 1550-1653 New!
Regional map of Ireland and Northern Ireland showing the four provinces and regional clan associations around 1570. Edited by Samuel Rawson Gardiner, published by Longmans, Green, and Co. in 1892, and made available at Ancestry.com. Click the image to see the map in a larger version in a separate window.

1555:

Map of Central Europe
From the Atlas to Freeman's Historical Geography, edited by J.B. Bury, a map of the political divisions of Germany and Central Europe in the 1555, here at the Medieval History site.

1560:

Sengoku Daimyo Circa 1560
Very large, attractive map of Japan by Christopher West at the Samurai Archives site.

The Unification of Japan 1560-1590
Large, colorful map by Christopher West at the Samurai Archives site depicts the holdings of Nobunaga, Hideyoshi, and Ieyasu.

1563:

Map of the Baltic Lands
A map depicting the lands bordering the Baltic Sea, including Russia, Scandinavia and Northern Europe. From the Atlas to Freeman's Historical Geography, online here at the Medieval History site.

1569:

Polish-Lithuanian Commonwealth from the Union of Lublin, 1569 to 1667 New!
A clear black and white map showing the boundaries of Poland-Lithuania in 1569 and the boundary between Poland and Lithuania at the Union of Lublin also depicts fiefs and territories within and around the nation in the sixteenth and seventeenth centuries. From the Library of Congress Country Study on Poland, online here at the Medieval History site.

1570:

Ireland, ca. 1570
Regional map of Ireland and Northern Ireland showing the four provinces and regional clan associations around 1570. Edited by Samuel Rawson Gardiner, published by Longmans, Green, and Co. in 1892, and made available at Ancestry.com. Click the image to see the map in a larger version in a separate window.

1572:

Sengoku Daimyo Circa 1572
Very large, attractive map of Japan by Christopher West at the Samurai Archives site. 

1582:

Môri Holdings in Western Japan Circa 1582
Huge map of Western Japan by Christopher West at the Samurai Archives site. 

Shimazu Holdings in Kyushu Circa 1582
Simple map by Christopher West at the Samurai Archives site depicts the holdings of Shimazu Yoshihisa.

1583:

Japan after Nobunaga
Very large, attractive map of Japan by Christopher West at the Samurai Archives site. 

1600:

Ireland circa 1600 A.D.
Clear map of is followed by useful info at the Ireland's History in Maps site.

Sekigahara Campaign
Very well-annotated map by Christopher West at the Samurai Archives site depicts the holdings of the various clans involved in the Sekigahara conflict.