The Prince of Pereyaslavl was the ruler of the Principality of Pereyaslavl, a lordship based on the city of Pereyaslavl on the Trubezh River,^[1] and straddling extensive territory to the east in what are now parts of Ukraine. It was situated on the southern frontier of Kievan Rus' and bordered the steppe.

This article needs additional citations for verification. (June 2023)

The principality emerges was apportioned as the inheritance of Vsevolod Yaroslavich, son of Yaroslav the Wise; his brother Svyatoslav received Chernigov, while Smolensk went to Vyacheslav and Vladimir-in-Volhynia to Igor; this ladder of succession is related to the seniority order mentioned above.^[2] Vsevolod's appanage included the northern lands of Rostov and the lightly colonised northeast (see Vladimir-Suzdal).

The Primary Chronicle recorded that in 988, Vladimir had assigned the northern lands (later associated with Pereyaslavl) to Yaroslav.^[3] The town was destroyed by the Mongols in March 1239, the first of the great Rus cities to fall.^[4] Certainly from the reign of Vsevolod Yaroslavich, the princes of Pereyaslavl held the principality of Rostov-Suzdal, which was heavily colonized by Slavs thereafter, a process which strengthened the region's power and independence, separating the two regions.^[5]

In 1132, Yaropolk became Grand Prince on his brother Mstislav's death, while the Monomashichi descended into general internecine conflict over the Pereyaslavl principality. Yaropolk appointed Vsevolod Mstislavich, prince of Novgorod, to the principality of Pereyaslavl – in this era designated heir to the Kievan throne^[6] – thus provoking Yaropolk's younger brother Yuri Dolgoruki, controller of Suzdal, into war. Yuri drove out Vsevolod, whom Yaropolk then replaced with Izyaslav. An agreement was reached by 1134 between Yuri and Yaropolk that their common brother Vyacheslav would take the throne of Pereyaslavl.^[7]

• Yaroslav I the Wise, 988–1010
• Boris Vladimirovich
• Elias Yaroslavich, c. 1019
• —
• Vsevolod I, 1054–1076
• Rostislav I Vsevolodich 1076, d. 1093
• Vladimir I Monomakh, 1076–1078
• Rostislav I Vsevolodich (again), 1078–1093
• Vladimir II Vsevolodich (again), 1094–1113
• Svyatoslav I Vladimirovich, d. 1114
• Yaropolk I, 1114–1132
• Vsevolod II Mstislavich, 1132 x 1134
• Izyaslav I Mstislavich, 1132 x 1134
• Vyacheslav I Vladimirovich, 1132–1134
• Andrey Vladimirovich, 1135–1141
• Vyacheslav I Vladimirovich (again), 1142
• Iziaslav II, 1143–1145
• Mstislav Izyaslavich, 1146–1149
• Rostislav II Yurevich, 1149–1151
• Mstislav Izyaslavich (again), 1151–1155
• Gleb Yurevich, 1155–1169
• Vladimir III Glebovich, appointed 1169, died 1187
• Yaroslav II Mstislavich ??
• Vsevolod III the Big Nest, ?–1206
• Vsevolod IV Svyatoslavich, 1206
• Rurik Rostislavich, 1206–?
• Vladimir IV Rurikovich, 1206–1213