When did "awkwarde" mean "backhanded"?

Question

In an old tale about Robin Hood and Guy of Gisborne this can be read:

Robin thought on Our Lady deere,
And soone leapt vp againe,
And thus he came with an awkwarde stroke;
Good Sir Guy hee has slayne.

In this text, the word awkwarde means "backhanded", as noted by this Tom Sawyer excerpt:

“Why, that ain’t anything. I can’t fall; that ain’t the way it is in the book. The book says, ‘Then with one back-handed stroke he slew poor Guy of Guisborne.’ You’re to turn around and let me hit you in the back.”

Looking at the etymology of awkwarde (currently awkward), the Etymonline web page says that awkward comes from awk 'back-handed'. Fine, but it also says that awk meant "turned the wrong way" in the 15th century. It comes

from Old Norse afugr "turned backwards, wrong, contrary"

OK, so in Old Norse it did mean "turned backwards" but it seems that in English it implied a "wrong" side instead of just a "back" side.

So I would like to know:

• Was the back of the hand considered the "wrong" side of the hand by the 15th century? Or is it that the word "wrong" may mean just "back"? Or may it imply that the back of the hand is the "wrong" (in the sense of "clumsy") side of the hand (not the side you use to handle tools or weapons)?
• In which period did the word awkwarde mean "backhanded"? When did the word lose that meaning and came to mean just "not smooth or graceful" or "uncomfortable or abnormal"?

Answer 1

The sense appears to derive from awk that is the wrong way round suggesting the back of the hand as the "improper" way to show or use your hand like in slapping or beating with the back of your hand:

From Grammarphobia:

• John Ayto, in his Dictionary of Word Origins, says “awkward” was coined in the 1300s in Scotland and northern England, where it meant “turned in the wrong direction.”

• Ayto writes that it’s a combination of the Middle English adjective “awk” (“the wrong way round, backhanded”) and the directional suffix “-ward.”

• Ayto doesn’t give any citations for the Scottish and northern English origins of “awkward.” But the earliest example of the word in the OED is from a manuscript that includes words in the Northumbrian dialect spoken in the north. The medieval Kingdom of Northumbia covered what is now northern England and southeastern Scotland.

• Oxford says “awkward” meant “in the wrong direction, in the wrong way,” when it appeared for the first time in the Middle English poem Pricke of Conscience (1340): “Þe world þai all awkeward sette” (“They turned the world all awry”).

The sense of "not graceful" appeard later, in the 16th century

• The “clumsy” sense of “awkward” showed up a few years later. The OED’s earliest example is from John Palsgrave’s L’Esclarcissement de la Langue Francoyse (1530), a French-English grammar:

• “Awkwar leftehanded, gauche.” (At the time, “left-handed” meant “clumsy” as well as “using the left hand more naturally than the right.”)