Short answer- yes, so let's just look for reasons why such mistake happen.

Voronezh and Oryol at the time were border fortresses, part of the Great Abatis Border (Большая засечная черта)- a chain of fortifications protecting Muskovy from Tartaric raids, originally constructed by Ivan the Terrible. Oryol was established by him. Voronezh was a latter addition, added to southern defenses in 1585-1586. Then it was burned down in 1590 and had to be rebuild in 1594.

The map in picture was made in Holland by Hessel Gerritsz in 1613 using Fyodor Godunov's map as a basis. Hence there is at least two layers.

We do not know much about Boris original or circumstances of its making. One of the proposed theories is that it was training practice during princes education (essentially homework assignment), rather some serious work of cartography, because the map seems to be based on Merkator's map of Russia made in 1595 and is ignorant of local cartography, mainly The Great Drawing (Большой чертёж) made under Ivan the Terrible. Also Boris original was of the smaller scale, ending at the south with region of the Abatis Border.

Hessel Gerritsz not only expanded, but also updated the map with recent data. Fyodor's life falls in to the period of Russian history called Smuta (Смута) that kicked off with full force in early 1600's with great famine, appearance of some guy claiming to be son of Ivan the Terrible, who managed to gain support in Polish-Lithuania. The decade long civil war went in full swing, with total of 4 "sons of Ivan the Terrible" making an appearance.

Both Voronezh and Oryol supported first two (and only important) "sons". Oryol even served as residence Lzhedmitriy II for a time as south-east Russia was his power base in general in large part due to much of his support base being Tatars. By the end of Lzhedmitriy II's "reign" closest thing to allies he had was Uraz-Mohammed, Qasim Khan and Piotr Urusov (born Urak Yanarslan uly)- Nogay princeling raised in Moskow court, who brought force of "service Tatars" to Lzhedmitriy. In November of 1610 Lzhedmitriy killed Uraz-Mohammed (after learning about his plans to betray him) and soon was himself killed by Urusov in revenge.

Urusov, now an independent warlord in his own right, retreated south in to Astrahan and found yet another "son of Ivan the Terrible" (Lzhedmitriy IV), but soon abandoned this scheme and entered service of Crimea Khan in 1612 (interestingly, Urusov's father Yak-Arslan become new Qasim Khan and remained loyal to Moskow).

Given that map is made few years after Lzhedmitriy II demise, notion that "remains of Lzhedmitriy force went over to Crimea" was understood as "his holdings are now controlled by Crimea" by Dutch cartographer seems as most likely conclusion.

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Literature:

About the map:

Багров Л. C. История русской картографии. — М.: Центрполиграф, 2005

About the deaths of Uraz-Mohammed and Lzhedmitriy II:

Конрад Буссов. Московская хроника. 1584-1613. — М.-Л.: АН СССР, 1961.

Budziło J. Wojna moskiewska wzniecona i prowadzona z okazji fałszywych Dymitrów od 1603 do 1612 r. Wrocław: Wydawn. Uniwersytetu Wrocławskiego, 1995.