Based on a comment by community member "mins", I took a look around. Mins initially thought it was the Lockheed Electra Model 10, but that didn't look quite right to me. "Mins" later edited their comment to include the Model 14, so I performed some searching, and I think the cribbage board features a Lockheed 14-WF62 Super Electra.

If you look at the photo on this page on Airliners.net, you can see a striking resemblance to the aircraft on the cribbage board.

I'm not sure of the fair use of the photo on that page, so I'll just link to it here.

Most of the credit for this answer goes to "mins", because their suggestion is what helped me find this specific photo.

According to the caption on Airliner.net:

Sold to the first British Airways in August 1939 as G-AFYU and crashed off Malta on 21 December 1939.

The use by British Airways in the late 1930's could possibly explain the presence of the Union Jack on the cribbage board.

Based on a comment by community member "mins", I took a look around. Mins initially thought it was the Lockheed Electra Model 10, but that didn't look quite right to me. "Mins" later edited their comment to include the Model 14, so I performed some searching, and I think the cribbage board features a Lockheed 14-WF62 Super Electra.

If you look at the photo on this page on Airliners.net, you can see a striking resemblance to the aircraft on the cribbage board.

I'm not sure of the fair use of the photo on that page, so I'll just link to it here.

Most of the credit for this answer goes to "mins", because their suggestion is what helped me find this specific photo.

According to the caption on Airliners.net:

Sold to the first British Airways in August 1939 as G-AFYU and crashed off Malta on 21 December 1939.

The use by British Airways in the late 1930's could possibly explain the presence of the Union Jack on the cribbage board.

Based on a comment by community member "mins", I took a look around. Mins initially thought it was the Lockheed Electra Model 10, but that didn't look quite right to me. "Mins" later edited their comment to include the Model 14, so I performed some searching, and I think the cribbage board features a Lockheed 14-WF62 Super Electra.

If you look at the photo on this page on Airliners.com, you can see a striking resemblance to the aircraft on your cribbage board.

I'm not sure of the fair use of the photo on that page, so I'll just link to it here.

Most of the credit for this answer goes to "mins", because their suggestion is what helped me find this specific photo.

Based on a comment by community member "mins", I took a look around. Mins initially thought it was the Lockheed Electra Model 10, but that didn't look quite right to me. "Mins" later edited their comment to include the Model 14, so I performed some searching, and I think the cribbage board features a Lockheed 14-WF62 Super Electra.

If you look at the photo on this page on Airliners.net, you can see a striking resemblance to the aircraft on the cribbage board.

I'm not sure of the fair use of the photo on that page, so I'll just link to it here.

Most of the credit for this answer goes to "mins", because their suggestion is what helped me find this specific photo.

According to the caption on Airliner.net:

Sold to the first British Airways in August 1939 as G-AFYU and crashed off Malta on 21 December 1939.

The use by British Airways in the late 1930's could possibly explain the presence of the Union Jack on the cribbage board.