This study examined whether speech-on-speech masking is sensitive to variation in the degree of similarity between the target and the masker speech. Three experiments investigated whether speech-in-speech recognition varies across different background speech languages (English vs Dutch) for both English and Dutch targets, as well as across variation in the semantic content of the background speech (meaningful vs semantically anomalous sentences), and across variation in listener status vis-à-vis the target and masker languages (native, non-native, or unfamiliar). The results showed that the more similar the target speech is to the masker speech (e.g., same vs different language, same vs different levels of semantic content), the greater the interference on speech recognition accuracy. Moreover, the listener’s knowledge of the target and the background language modulate the size of the release from masking. These factors had an especially strong effect on masking effectiveness in highly unfavorable listening conditions. Overall this research provided evidence that that the degree of target-masker similarity plays a significant role in speech-in-speech recognition. The results also give insight into how listeners assign their resources differently depending on whether they are listening to their first or second language