Cropper had several trials in England, including with Wolverhampton Wanderers and Leicester City, before joining the Ipswich Town academy in 2010.[3] He made the bench for the Ipswich first team, but suffered a torn meniscus.[4] He failed to receive a new contract offer from Ipswich and was released after the 2011–12 season.
Southampton
Cropper joined Southampton in August 2012.[4][5] Cropper served as a backup keeper for the Saints; making the first team bench, but playing for the U-21 and U-23 teams and never making a first team appearance. His time with Southampton included multiple injuries.[6][7] After three years at the south coast club, Cropper was released in May 2015.[8]
Milton Keynes Dons
On June 30, 2015, Cropper joined newly promoted Championship side Milton Keynes Dons.[9] He made his debut for MK Dons on August 11, 2015, in an EFL Cup first round win against Leyton Orient.[10][11] In September Cropper underwent knee surgery that kept him sidelined for over a month.[12] On April 16, 2016, Cropper was sent off for a foul on Preston North End's striker Eoin Doyle.[13] He returned from the suspension on April 23 and suffered a season ending shoulder injury in a 4–1 loss to Brentford.[14] Cropper was released after the 2015–16 season when the club decided not to take up the one-year option in Cropper's contract after being relegated to League One.[15]
The Revolution's first choice goalkeeper, Bobby Shuttleworth, was traded to Minnesota United ahead of the 2017 season, giving Cropper a shot at the starting job. Cropper impressed head coach Jay Heaps and won the starting job coming out of preseason.[18] He started 28 of the 34 league games during the year, keeping eight clean sheets.[19] However the Revolution finished in 7th place in the Eastern Conference, missing out on the playoffs by five points.[20]
Cropper did not play during the 2018 season. He missed the start of the season due to a concussion. When he had returned to action, head coach Brad Friedel kept Matt Turner as the starter with Brad Knighton as the second choice keeper.[21][22][23]
Cropper made his first appearance of 2019 on March 30, a 2–1 win over Minnesota United in the 5th game of the season.[22] He would start the next 7 games for the Revs before Friedel decided to bench him. Bruce Arena came in as the new head coach, but Cropper failed to return to the lineup.[24]
Hartford Athletic (loan)
On August 17, 2019, Cropper was loaned to USL Championship side Hartford Athletic for the remainder of the season.[25] He made his debut for Hartford on August 24, a 3–2 win over Atlanta United 2. Cropper started the final nine games of the season for Hartford, keeping one clean sheet.[24]
On November 21, 2019, New England declined their contract option on Cropper.[26]
Houston Dynamo
On January 24, 2020, Cropper signed with MLS club Houston Dynamo.[27] He did not make any appearances for the Dynamo in 2020, serving as the backup for Marko Marić.[28] His contract option was declined by Houston following their 2020 season.[29]
FC Cincinnati
On December 30, 2020, it was announced that Cropper had signed for FC Cincinnati ahead of their 2021 season.[30] On August 27, 2021, Cropper was loaned to USL Championship side Memphis 901.[31] He was waived by Cincinnati on September 15, 2021.[citation needed]
Vancouver Whitecaps
On March 15, 2022, Cropper was signed as a free agent by the Vancouver Whitecaps FC. He was signed for the 2022 season with a club option for 2023.[32][33]
Orange County SC
On March 14, 2023, Cropper signed with USL Championship side Orange County SC.[34] On July 4, 2023, Cropper retired from playing professionally and become an assistant coach at University of St. Thomas.[35]