Wideband tympanometry (WT) measurements provide a view of the acoustic response properties of the middle ear over a broad range of frequencies and ear-canal pressures. These measurements show sensitivity to trends in ear-canal/middle ear maturation and changes in middle ear status as a result of different types of dysfunction. While results from early WT work showed improvements over ambient wideband tests in terms of test performance for identifying middle ear dysfunction and conductive hearing loss (CHL), more recent studies have shown high, but similar test performance for both ambient and tympanometric wideband tests. Case study and group results presented in this article, demonstrating the sensitivity of WT to middle ear dysfunction, CHL, and maturational changes in the middle ear, are promising and suggest the need for additional investigations in individual subjects and large subject populations. Future research should focus on identifying key predictors of developmental trends, middle ear dysfunction, and CHL in an effort to develop middle ear tests with high sensitivity and specificity. Technological advances, more accessibility to equipment, and evolving data analysis techniques should encourage progress in the areas of WT research and clinical application.