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Police believe the gang drilled upwards through a ceiling and then "burrowed" through several layers of wooden flooring to gain access to the display case at the Royal Lancers and Nottinghamshire Yeomanry Museum in Newark.
Among the items stolen were a polo trophy, a cavalry trumpet and several statuettes of mounted soldiers.
A parcel-gilt rosewater dish - said to be a sister piece to the Wimbledon women's singles trophy - was also taken.
Officers are appealing for help in tracking down the "distinctive" historical haul following the raid, which is believed to have happened in the early hours of Sunday 29 October.
Museum curator Steve Cox said: "It's disgusting that they've taken history from the people who have served and fought for this country.
"The items they have taken are priceless to the museum. How do you put a value on history?"
He added: "We're upset about it, but we're fighting back and we're going to rebuild from what's gone."
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Detective Inspector Luke Todd, of Nottinghamshire Police, said: "This was an audacious, planned, and targeted attack on what is a wonderful historic building and was clearly very well organised.
"The items that were stolen are not only high in monetary value but also high in sentimental value not only to the military, but also to the wider community in the area.
"These items are worth so much more to the museum than they are melted down in their silver form."
The force appealed for anyone who "may have seen anything suspicious or has heard about someone trying to sell items like this" to get in touch.
Detective Inspector Todd added: "These criminals may think they've got away with a lot of silver at this moment in time, but they definitely haven't got away with the crime."
Officials also said a search of the site had confirmed none of the museum's guns or other weaponry had been stolen in the heist.