1920s trophy cups. Not your standard loving cup sort of thing. Sterling silver, American and British.

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Cut-glass and silver trophy cup with horn handles. Cut-glass is straight and spread with cut vertical ornament in the motif of alternating flutes and circles and a star cut to the underside. Silver collar with a flared rim and tooled leaf and berry bottom rim. Horn handles carved in the motif of animals sprouting their own horns with silver mounts. ca. 1910. American. Sterling silver, cut-glass and horn. Maker’s marks: fully marked including indistinct maker’s stamp (probably Redlich). Image © 1stdibs.com, Inc. 2020. Fair use license. via https://www.1stdibs.com/furniture/dining-entertaining/sterling-silver/antique-american-cut-glass-trophy-carved-big-game-alpha-antlers/id-f_19997302/
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Trophy cup for the Lake Michigan boat race Challenge Cup (flag detail). Tall urn design with three high-looping handles and a domed foot with garland decoration applied to the top of the urn and flowers and shells applied to the foot. Reeded rim. 1907. American. Sterling Silver. Engraved “Challenge cup for the annual competition among launches on Clark Lake, Michigan” on the front. Inscribed “Presented to the Clark Lake Yacht Club by Chauncey F. York, 1907.” 1907. American. Sterling silver. Maker’s marks: fully marked with maker’s mark for Redlich and a retailer’s mark for Bailey, Banks and Biddle. Number 4684. Image © 1995-2020 eBay Inc. Fair use license. via https://www.ebay.com/itm/143648679455
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Silver hydroplane boat race trophy with the bowl having wing mounted and leaf wrapped caryatid side handles. Applied enamel flags and circular and wreathed frames, one inset with a chased motorboat in churning water and the other being engraved “Presented by Sir Thomas J. Lipton Bart. KCVO to the National Yacht Club of Toronto for competition in outboard hydroplane races at the Canadian National National Exhibition Regatta 1929.” Baluster shaft with acanthus leaves and scrolled brackets with a raised foot with scalloping. Raised cover with a cast finial in the design of a nude angel lunging forward with one arm while clutching her drapery with the other. 1919. George V. Sterling silver. Made in London in 1929. Hallmarked. Image © 1995-2020 eBay Inc. and Nelson and Nelson Antique Silver. Fair use license. via https://www.ebay.com/itm/George-V-Trophy-Cup-Art-Deco-Hydroplane-Boat-Race-English-Sterling-Silver/143480968785?_trkparms=aid%3D1110002%26algo%3DSPLICE.SOI%26ao%3D1%26asc%3D20190711095549%26meid%3Ddca160768a9949b28e50d768bb096cb7%26pid%3D100047%26rk%3D2%26rkt%3D12%26sd%3D143648679455%26itm%3D143480968785%26pmt%3D1%26noa%3D1%26pg%3D2047675%26algv%3DSellersOtherItemsV2%26brand%3DGoldsmiths+%26+Silversmiths&_trksid=p2047675.c100047.m2108