Production and use of sweet olive ( Osmanthus armatus ), fragrant tea olive ( O . fragrans ), holly tea olive ( O . heterophyllus ), and fortune’s osmanthus ( O . x fortunei ) as a landscape plant is currently limited to U.S. Department of Agriculture (USDA) Hardiness Zones 7 to 10, and nursery growers wish to extend the range of these species into colder climates. To provide recommendations to growers and landscapers and inform breeding efforts for cold-hardiness improvement, a replicated trial was conducted in a USDA Hardiness Zone 6b/7a transition zone. Fifteen cultivars and two unnamed accessions representing four species were evaluated for growth, stem necrosis, and flowering in a pot-in-pot production system from 2015 to 2017. One-half of the plants in each cultivar were moved to winter protection each November and returned to the field each May. There were significant differences in growth and cold-hardiness among cultivars. Percent increase in the growth index after three growing seasons for winter-exposed accessions of sweet olive, fortune’s osmanthus, fragrant tea olive, and holly tea olive averaged 867%, 1175%, 155%, and 6361%, respectively. Percent stem necrosis in May 2017 for sweet olive, fortune’s osmanthus, fragrant tea olive, and holly tea olive averaged 1.1%, 2.7%, 44.8%, and 20.2%, respectively. The most cold-tolerant accessions based on stem necrosis and growth index of winter-exposed plants were ‘Kaori Hime’, ‘Hariyama’, ‘Shien’, ‘Head-Lee Fastigate’, and ‘Rotundifulius’ holly tea olive, ‘San Jose’ fortune’s osmanthus, and ‘Longwood’ sweet olive. Of these cultivars, Kaori Hime, San Jose, and Longwood flowered under winter-exposed conditions. All fragrant tea olive cultivars were damaged by winter exposure. ‘Fodingzhu’ was the only fragrant tea olive cultivar that flowered each year under winter-exposed conditions. Evaluation and breeding efforts are continuing to extend the range for production and growth of this genus.