The copy of the first Oor Wullie annual could go for as much as £4500 when it goes on sale on Tuesday.
Several others will be up for auction alongside the 1941 edition including Oor Wullie and The Broons annuals from between 1941 and 1957.
War propaganda drawings by Dudley D Watkins, featuring Lord Snooty, are first to go under the hammer.
Steven Dewar of Curr and Dewar Auctioneers described the 1941 annual as in good condition.
Its owner wishes to remain anonymous but revealed that the collector’s item has been passed down through three generations.
They were gifted to the seller’s grandfather by a friend who was an advertising manager at Dundee-based publishers DC Thomson, the printer of the comics and annuals.
“The vendor had seen one or two of the first ever annuals sold and thought to himself ‘I’m sure I’ve got one of them’.
“He looked it out and took it to the Antiques Road Show when they were in this area and asked if it was the real thing, and they said ‘yes, it’s genuine’.”
Interest in the annual is already high due to its good condition and lack of wear and tear.
Mr Dewar added: “Once this is bought it will probably be put away and not come out again for a generation. This one came out right at the beginning of the Second World War. It’s an artefact of its time.
“It’s an investment item and is only going to increase in value. It was one of the first ever issues of what became an iconic brand.
“I’m aware of a few selling over the past few years but this is our first one. One sold in 2014 for £4400 and one sold in December last year for £3400 but it all depends on the condition they’re in.
“This one is in good condition and there’s no doubt any collectors of the Oor Wullie memorabilia will want to have this as pride of place in their collection.”