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I don't know that the image was explicitly labeled "Ao & Tiamat" (spoiler: it wasn't), so it could have been almost any giant humanoid, playing a board game with a multi-headed† draconic creature.
(†Turns out, it isn't multi-headed. Thanks to Quadratic Wizard for pulling this archaic image out of their hat!)

The board was circular, with a few grid lines, & a few pieces similar to chess pieces were in play.

The image was black & white, similar to a pencil drawing or wood cut. (The level of detail was not high.)

It was for an older version of D&D, & I have since seen the image referenced, but cannot find it now.

I would love to know who drew it, & whether it was supposed to relate to Xorvintaal. I would like to at least know which book to find it in!?

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    \$\begingroup\$ Can you narrow it down to a year range? D&D or AD&D? TSR/WotC or third-party? Book or magazine? \$\endgroup\$ Commented May 17 at 21:22
  • \$\begingroup\$ The first that comes to mind is the black and white illo of a Riddlemaster bard playing chess with a normal dragon in the 2e complete bard's handbook. Not Ao, not Tiamat, not a circular board, though. \$\endgroup\$
    – Kirt
    Commented May 18 at 4:20
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    \$\begingroup\$ Long shot question: Are you sure it wasn't a magazine cover? \$\endgroup\$
    – Novak
    Commented May 19 at 18:24
  • \$\begingroup\$ @QuadraticWizard Given the art & print style, I'm fairly certain it was pre-WotC; I don't recall any color in the whole book. \$\endgroup\$ Commented May 20 at 0:54
  • \$\begingroup\$ @Kirt Even though I never owned that book, I got excited... but no, that's not it; the draconic was on the left & no larger than the humanoid on right & the board definitely featured a circular ring pattern. \$\endgroup\$ Commented May 20 at 0:59

1 Answer 1

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This one? Giantcraft (1995), p.8

Giantcraft p.8

This image meets most of your requirements: a humanoid potentially interpreted as giant, playing a chess-like game with a dragon, on a circular board with grid lines, black and white, and from an older edition of D&D (AD&D 2e).

However, contrary to your description, the dragon is on the right, and not multi-headed.

This particular image is unrelated to Xorvintaal. According to the Forgotten Realms Wiki page on Xorvintaal, it was introduced in the late-3.5 Monster Manual V (2007). It also doesn't represent Tiamat, since the dragon has only one head, and doesn't represent Ao, who according to his Forgotten Realms Wiki entry rarely takes humanoid form, and has white hair and beard when he does.

In fact, even if this isn't the image, it's unlikely that any black and white art represents Xorvintaal: by the time it was introduced in late 3.5, all WotC D&D books and even the Paizo magazines used color art more or less exclusively, and no other published sourcebook would have copyright permission to use Xorvintaal (although potentially it may have appeared in something other than a sourcebook, like a fan work or novel).

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    \$\begingroup\$ This is it! The dragon is... different in a lot of ways, from what I could recall. The art is also higher detail than I'd thought. I think the stump in the foreground is intended as a clue that the creatures are giant. Giantcraft is among the books I've misplaced; but the image tells me everything I needed to know about the board. (I am definitely taking inspiration from that layout!) Thank you, magical Quadratic Wizard of ancient Arcana checks! \$\endgroup\$ Commented May 22 at 17:19
  • \$\begingroup\$ I will edit the Question to note that it's (almost) definitely not Tiamat. \$\endgroup\$ Commented May 22 at 17:21
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    \$\begingroup\$ Another great answer from the Encyclopedia Quadratica 😁 \$\endgroup\$ Commented May 22 at 17:48

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