This study examines the impact that education has on wages earned by male private sector workers in Trinidad and Tobago and its evolution during 1980-2000. Using Individual Population Census data for 1980, 1990 and 2000, the wage returns of men derived from their relevant years of schooling is estimated by using both the Quantile Regression (QR) and Instrumental Variable Quantile Regression (IVQR) methodology. This study reveals that the 1983-1993 economic recession may have been responsible for decline in the overall returns to schooling, as well as the returns of men qualified at the secondary and university level during 1980-1990. However, as Trinidad and Tobago entered a period of economic prosperity during 1994-2008, the overall returns to schooling, as well as the returns to university-level schooling, improved in 2000. In spite of this, the wage returns of men qualified at the secondary level continued to fall in 2000. This implies that the influx of university schooled men in 2000 may have crowded out the job opportunities suited towards those who have secondary-level schooling.