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Description
I did a ton of research for this map. Unfortunately most of the sources for "conquered areas" comes from accounts such as:

consisting largely of mountains, moorland and forests, were bounded on the north by the Minho River, and on the south by the Mondego RiverSo there was a slight amount of guess work to be done especially when it came to conquests of cities; where the city limit was quite vague during the 10-12th centuries.

It was extremely interesting to read about Portuguese history and the political situations leading to the modern borders of Portugal. For instance "Portugal was obliged to surrender as his ransom almost all the conquests Afonso Henriques had made in Galicia (north of the Minho River) in the previous years." And that's why the northern border of Portugal looks so strange... because it was a ransom.
The city of Olivenza is still contested to this day due to a treaty from the 1800's that was drafted during the Napoleonic wars but repealed following the defeat of Napoleon.
Sancho I conquered all the way to Silves, only to lose all of the lands south of the Tejo river due to in-fighting with other Christian kingdoms most notably Leon-Castile which had forged an alliance with the Almohads; to combat Portuguese expansionism in Iberia.

Notes:
I was interested in trying to differentiate my style with regards to pages being visible in the end product. The original concept was supposed to have all the border progressions on the topographic map but it was too clustered and nearly impossible to implement.
Thanks to and for tips with the creation of this map. A Special thanks to Angelo my Portuguese friend who helped me with finding facts and other details about Portugal

If you would like to download the full sized version, consider becoming a Patreon all of my full sized and original files are on there for donators + more perks!

Sample References:

He was named a count and given control of the frontier region between the Limia and Douro rivers by Alfonso III of Asturias. 868

The regions to its south were only again conquered in the reign of Ferdinand I of León and Castile, with Lamego falling in 1057, Viseu in 1058 and finally Coimbra in 1064.

in 1095, Portugal broke away from the Kingdom of Galicia. Its territories, consisting largely of mountains, moorland and forests, were bounded on the north by the Minho River, and on the south by the Mondego River.

Condado Portucalense, known at the time as Terra Portucalense or Província Portucalense,[6] which would last until Portugal achieved its independence, recognized by the Kingdom of León in 1143. Its territory included much of the current Portuguese territory between the Minho River and the Tagus River.

In 1169 the now old Dom Afonso was possibly disabled in an engagement near Badajoz by a fall from his horse, and made prisoner by the soldiers of the king of León Fernando II also his son-in-law. From this time onward, the Portuguese king never rode a horse again, but it is not certain this was because of the disability: according to the later Portuguese chronistic tradition, this happened because Afonso would have to surrender himself again to Fernando II of León or risk war between the two kingdoms if he rode a horse. Portugal was obliged to surrender as his ransom almost all the conquests Afonso had made in Galicia (north of the Minho River) in the previous years.

Description
I did a ton of research for this map. Unfortunately most of the sources for "conquered areas" comes from accounts such as:

consisting largely of mountains, moorland and forests, were bounded on the north by the Minho River, and on the south by the Mondego RiverSo there was a slight amount of guess work to be done especially when it came to conquests of cities; where the city limit was quite vague during the 10-12th centuries.

It was extremely interesting to read about Portuguese history and the political situations leading to the modern borders of Portugal. For instance "Portugal was obliged to surrender as his ransom almost all the conquests Afonso Henriques had made in Galicia (north of the Minho River) in the previous years." And that's why the northern border of Portugal looks so strange... because it was a ransom.
The city of Olivenza is still contested to this day due to a treaty from the 1800's that was drafted during the Napoleonic wars but repealed following the defeat of Napoleon.
Sancho I conquered all the way to Silves, only to lose all of the lands south of the Tejo river due to in-fighting with other Christian kingdoms most notably Leon-Castile which had forged an alliance with the Almohads; to combat Portuguese expansionism in Iberia.

Notes:
I was interested in trying to differentiate my style with regards to pages being visible in the end product. The original concept was supposed to have all the border progressions on the topographic map but it was too clustered and nearly impossible to implement.
Thanks to and for tips with the creation of this map. A Special thanks to Angelo my Portuguese friend who helped me with finding facts and other details about Portugal

If you would like to download the full sized version, consider becoming a Patreon all of my full sized and original files are on there for donators + more perks!

Sample References:

He was named a count and given control of the frontier region between the Limia and Douro rivers by Alfonso III of Asturias. 868

The regions to its south were only again conquered in the reign of Ferdinand I of León and Castile, with Lamego falling in 1057, Viseu in 1058 and finally Coimbra in 1064.

in 1095, Portugal broke away from the Kingdom of Galicia. Its territories, consisting largely of mountains, moorland and forests, were bounded on the north by the Minho River, and on the south by the Mondego River.

Condado Portucalense, known at the time as Terra Portucalense or Província Portucalense,[6] which would last until Portugal achieved its independence, recognized by the Kingdom of León in 1143. Its territory included much of the current Portuguese territory between the Minho River and the Tagus River.

In 1169 the now old Dom Afonso was possibly disabled in an engagement near Badajoz by a fall from his horse, and made prisoner by the soldiers of the king of León Fernando II also his son-in-law. From this time onward, the Portuguese king never rode a horse again, but it is not certain this was because of the disability: according to the later Portuguese chronistic tradition, this happened because Afonso would have to surrender himself again to Fernando II of León or risk war between the two kingdoms if he rode a horse. Portugal was obliged to surrender as his ransom almost all the conquests Afonso had made in Galicia (north of the Minho River) in the previous years.