Board Thread:Questions and Answers/@comment-1189400-20181110124135/@comment-1189400-20181209042514

The First and Second Bulgarian Empire. The default art for historical Bulgarian countryballs (three lions passant guardant sable langued gules on or) is based on the personal coat of arms of its last ruler, which appeared in armorial rolls after his supposed death.

Known coats of arms or royal insignias:

First Empire (681-1018):

803-814: a shield of a soldier in Khan Krum's army is depicted with a red crescent on blue

852-893: Pope Nicholas writes to newly baptized Prince Boris I that "the Holy Cross" must be used as a battle standard

893-927: A seal attributed to Tsar Simeon I depicts a lion or leoprd rampant.

997-1014: reconstruction of Tsar Samuil's funeral garment shows two perched birds, either eagles or peacocks, encircles by olive branches

Second Empire (1185-1395/1422):

1196-1207: remains of Tsar Kaloyan's garment in his grave depict golden double-headed eagles; a signet ring with an inscription "Kaloyan's ring" depicts a quadruped rampant, possibly leopard, but it's unknown if it belonged to Tsar Kaloyan

1256 - Armorial Gelre: "Keyser von Bolgherie" (Coloman II Asen) Barry of six (Or and Vert) with a canton of Romania (Latin Empire of Constantinople): Gules, a cross between four crosses patée encircled Or

1246-1257, Church of Taxiarchis Myhtropoleos, Castoria, Greece: mural portrait if Michael II Asen depicts him wearing a green garment patterned with golden one-headed eagles

1257-1277 - Boyana Church fresco: Constantine Tikh Asen is depicted with a cloak adorned with golden one-headed eagles and lions passant

1257-1322: Konstantin Tikh Asen and Theodor Svetoslav Terter issued coins with a big Latin cross pattée

1257-1330: coins of Constantine Tikh Asen, Georgi I Terter, Georgi II Terter and Mihail III Shishman Asen depict them holding a banner party per pale, cross sinister; those are all imitations of Venetian grosso

1295 - Lord Marshal's Roll: The "Roy de Bulgarie" (in 1290-1298 that is Smilets, before him Georgi I Terter in 1278-1290) has for a coat of arms lion rampant guardant, on sable, royally crowned or

1300-1322: Theodor Svetoslav Terter minted coind with a double-headed eagle

1340 (allegedly) - Fojnica roll - Lion rampant, gules on or

1331-1371: Ivan Alexander issued coins with a double-headed eagle

1375 -  Catalan atlas - flag drawing damaged, something golden

1371-1395: Ivan Shishman issued coins with a lion rampant.

14th century - Catalan atlas, another version - unclear symbols, circle or crescent, to the right of it an oblong symbol, possibly cross, both or on gules

14th century (1356-1371) - London Tetragospel: Portrait of Tsar Ivan Alexander shows him stepping on a red pillow with a golden double-headed eagle

End of 14th century (1371-1395) - anonymous Arab traveller's drawing of a shield of a soldier in Tsar Ivan Shishman's guard: Three lions rampant guardant, gules on or

1380 - Guillem Soler portolan: Ivan Shishman's monogram (Ш), gules on or, similar to an inverse Byzantine flag

Despotate/Tsardom of Vidin (1256-1422):

1256 (Yakov Svetoslav) - Gelre armorial: Quarterly of Romania (Constantinople/Latin Empire) and Azure

1325 - portolan of Angelino Dalorto: Mihail III Shishman Asen's monogram (Ш with a diagonal upward branch from the middle vertical line) gules on argent

1356-1396: Ivan Sratsimir issued coins with a double-headed eagle

14th century - Book of Knowledge: white flag with four red squares

Despotate of Dobruja/Dobrogea:

1386-1387: Ivanko Terter minted coins with a double-headed eagle

Later sources:

1438-1450 - Ulrich von Richental: "Kayser von bulgari" (Fruzhin Asen, claimed Tsar of the Tarnovo Tsardom) has for a sigil three lions passant guardant, sable on or (DEFAULT ART); Pullgarie der allt k.d. (Constantine II, claimed Tsar of the Vidin Tsardom) Or, a bull’s head, a cross potent between its horns, Gules. (This one, along with both the three lions passant sable on or and the gules lion rampant on or, appear in later armorials)

1559 - portolan of Bartolome Olives: field of or party per cross gules, in each canton the letter ω (or more likely Ш) gules

16th c. Unknown armorial (Bayerische Staatsbibliothek, München, Hss Cod.icon. 392d, Fol. 54v): Fruzhin and Constantine II are referred to, respectively, as "Der Keyser von Bulgary" (the emperor of Bulgaria) and "Der ander Keys[er] aus derTartarii" (the other emperor from the Tartaria): three lions passant guardant, sable on gules, and three lions passant guardant, gules on sable, respectively.

TL;DR. It's a mess. What do I do?