With the growing need to maintain roadway systems for provision of safety and comfort for travelers, network level decision-making becomes more vital than ever. In order to keep pace with this fast evolving trend, highway authorities must maintain extremely effective databases to keep track of their highway maintenance needs. Florida Department of Transportation (FDOT), as a leader in transportation innovations in the U.S., maintains Pavement Condition Survey (PCS) database of cracking, rutting, and ride information that are updated annually. Crack rating is an important parameter used by FDOT for making maintenance decisions and budget appropriation. By establishing a crack rating threshold below which traveler comfort is not assured, authorities can screen the pavement sections which are in need of Maintenance and Rehabilitation (M&R). Hence, accurate and reliable prediction of crack thresholds is essential to optimize the rehabilitation budget and manpower. Transition Probability Matrices (TPM) can be utilized to accurately predict the deterioration of crack ratings leading to the threshold. Such TPMs are usually developed by historical data or expert or experienced maintenance engineers' opinion. When historical data are used to develop TPMs, deterioration trends have been used vii indiscriminately, i.e. with no discrimination made between pavements that degrade at different rates. However, a more discriminatory method is used in this thesis to develop TPMs based on classifying pavements first into two groups. They are pavements with relatively high traffic and, pavements with a history of excessive degradation due to delayed rehabilitation. The new approach uses a multiple non-linear regression process to separately optimize TPMs for the two groups selected by prior screening of the database. The developed TPMs are shown to have minimal prediction errors with respect to crack ratings in the database that were not used in the TPM formation. It is concluded that the above two groups are statistically different from each other with respect to the rate of cracking. The observed significant differences in the deterioration trends would provide a valuable tool for the authorities in making critical network-level decisions. The same methodology can be applied in other transportation agencies based on the corresponding databases.