The issue of the influence of rootstock on winter-hardiness of plum (Prunus × rossica Erem.) tree flower buds in the Baltic region is becoming important. The choice of rootstock is the main precondition for obtaining a high yielding and sustainable plum orchard. Freezing of flower buds is one of the most significant damages in winter for stone fruits. The aim of the investigation was to determine the relationship between concentration of dry matter and reducing sugars in annual shoots during winter and wintering ability of trees. The dynamics of reducing sugar concentration in one-year-old shoots during winter was investigated during two successive seasons in two locations. Orchards were planted in 2001 in Latvia and in Estonia. The well-known plum cultivar ‘Kubanskaya Kometa’ (Prunus rossica Erem.) was grafted on eight clonal rootstocks (‘St. Julien A’, ‘Brompton’, ‘Ackermann’, ‘Pixy’, GF8/1, G5/22, GF655/2, and ‘Hamyra’) and eight generative propagated rootstocks (‘St. Julien INRA 2’, ‘St. Julien d’Orleans’, ‘St. Julien Noir’, ‘Brompton’, ‘Wangenheims Zwetsche’, ‘St. Julien Wädenswill’, ‘Myrobalan’ and Prunus cerasifera var. divaricate). Shoot samples were harvested two times during winter — at the end of January and at the end of March. Dry matter concentration (mg·g−1) and the concentration of reducing sugars (mg·g−1 DM) by Fehling’s solution method was determined. Tree flowering intensity was scored using a scale from 1 to 5, where 1 = no flowers and 5 = abundant flowering. Dry matter concentration in plum shoots varied among rootstocks, years and growing location. In Pūre, Latvia, the largest differences in dry matter concentration were found for trees grafted on ‘St. Julien INRA2’ (in 2011–2012) and ‘Brompton’ cuttings (in 2012–2013) but in Polli, Estonia for trees grafted on G5/22 (in 2011–2012) and ‘Myrobalan’ (in 2012–2013). One of the most stable rootstock/graft combinations in the trial when GF655/2 was used as rootstock, where dry matter concentration was between 491 and 525 mg·g−1, and reducing sugars between 37.5–49.2 mg·g−1, and flowering intensity between 2.5 and 4.