This research asked whether performance engendered by contextual control procedures would generalize to novel matching-to-sample stimulus arrangements. Two studies were conducted with young adult participants. In Study 1, participants first were trained to perform the contextually controlled conditional discrimination, X-AB, where the sample-comparison relations A1B1 and A2B2 were reinforced in the presence of contextual stimulus X1, but the relations A1B2 and A2B1 were reinforced in the presence of X2. Then, a new conditional discrimination, CD, was established via an unreinforced-conditional-selection procedure. Next, participants were tested for X-CD contextual control performance. Participants selected the originally established CD relations in the presence of X1, but the opposite relations in the presence of X2. Next, an additional conditional relation, EF, was established. Then, participants received trials consisting of entirely novel contextual stimuli, Z1 and Z2, and EF samples and comparisons. Selections were consistent with contextual control; that is, participants selected the originally established EF relations in the presence of one of the novel contextual Z stimuli, but selected the opposite EF relations in the presence of the other contextual Z stimulus. Study 2 systematically replicated these results with naive participants and demonstrated the necessity of first establishing a conditional discrimination prior to tests for generalized contextual control. The findings are discussed in terms of unreinforced conditional selection, stimulus classes, and new ways in which contextual control performances can emerge.