This study examined the relation of mathematics performance and gender with seven mathematics-related emotions (enjoyment, pride, anger, anxiety, shame, hopelessness and boredom) among adolescents. Using strict and lenient mathematics performance cut-off scores, respective groups of adolescents with mathematics difficulties (MD, n = 136), low (LA, n = 166) and typical mathematics performance (TA, n = 1056) were identified. Our results revealed that the MD group reported more shame than the LA group. The MD group also reported more negative emotions and less positive emotions than the TA group, with the exception of boredom, for which there was no statistically significant difference. The interaction effect between mathematics performance group and gender on emotions was significant. Only females with MD showed significantly higher levels of hopelessness and shame than females with LA, while males with LA even reported more boredom than males with MD. Concerning gender differences, males reported slightly more pride and enjoyment than females. However, the direction and magnitude of the gender differences showed great variance among mathematics performance groups. The practical implications of the results are discussed.