Recent studies have revealed that the frequency and magnitude of floods tend to increase due to climate change. Hence, excessive scouring due to flood events puts river bridges at greater risk of failure. This paper presents the initial findings of an experimental study to improve the understanding of the main characteristics of bridge pier scour under pressurized flow encountered during flooding. The experiments were carried out in four main groups according to two deck alignments with circular and oblong pier shapes. For each group of experiments, thirty-six tests were conducted under partially and fully pressurized flow conditions using four approach flow depths and three discharge values. The validity of the structured design approach for pier scour estimation implemented in the guidelines was investigated. The results showed that the bridge pier scour depths were up to 29.4% and 49.4% greater than the sum of the vertical contraction and local scour depths for 100 L/s for partially and fully pressurized flow conditions, respectively. However, as the discharge increased to 120 L/s, the bridge pier scour depth became 38.3% and 17.8% smaller than the sum of the vertical contraction and local scour depths for partially and fully pressurized flow, respectively. So, the structured design approach was determined to be safe for high discharge values. Furthermore, it was found that tests with a circular pier resulted in higher bridge pier scour depths than the sum of the vertical contraction and local scour depths up to 19.3% even for 120 L/s. Conversely, smaller bridge pier scour depths than the sum of the vertical contraction and local scour depths were observed up to 17.8% for tests with oblong piers. Thus, it can be concluded that the pier shape has a profound effect on scour holes and oblong piers cause smaller scour depths than circular piers in pressurized flow conditions. This study showed that the flow–pier–deck interaction significantly affects the depth and width of the scour hole, especially for small discharges and fully pressurized flow conditions.