Jamie Cleland joined the program ahead of the 2019 season.
Cleland helped guide Monmouth to one of the best seasons in program history in 2020-21 despite also navigating through the COVID-19 pandemic. The Hawks won the MAAC Championship as the No. 6 seed, and defeated Bowling Green in the first round of the NCAA Tournament. By the end of the season, Monmouth was receiving votes in the United Soccer Coaches Poll and had an RPI as high as 9. The team won four straight road games en route to the conference championship, including a game-winning goal in the 86th minute at No. 1 Quinnipiac. Under Cleland's guidance, Sean Murray was tabbed MAAC Co-Goalkeeper of the Year.