(1) Background: The aim of the present study was to assess the psychophysiological changes experienced by male academy soccer players in relation to venue. The team was matched to opponents who were deemed to be of a similar standard to the reference team; this was ascertained by the previous season’s league standing and coach ratings of opposition. (2) Methods: The sample comprised 14 male (Mage = 17.21, SD = .43) academy soccer players who competed for a Premier League Academy team. Salivary cortisol (C) and testosterone (T) levels were monitored at four time points (1 hour before, 30 minutes before, 30 minutes after and 1 hour after) across four competitive fixtures both at home and away, and a baseline training measure. Players also completed psychometric measures of sport emotion and social evaluation. (3) Results Findings showed that T was significantly higher after three defeats compared to training and the home win. Similarly, C was greater 30 minutes post-match compared to other timepoints. (4) Conclusions: In keeping with previous research, there were mixed findings in relation to anxiety and social evaluation. The current study provides further evidence that the relationship between endocrine responses, venue and psychological indicators are highly complex, and results may vary due to team levels, individual differences, opposition characteristics and venue.