North Ferriby United, Scarborough Athletic, Harrogate Town, Buxton (loan).
Ben Middleton joined the Pilgrims on an initial month's loan from Harrogate Town in December 2017. The defender, capable of playing at right-back or centre-half, emerged from Doncaster Rovers' youth set-up to make numerous appearances for North Ferriby United and Scarborough Athletic before a move to Harrogate Town in the summer of 2017. He had also spent a brief loan spell with Buxton prior to his arrival in Boston. After being recalled just days into his second month with the Pilgrims, Middleton returned for a fresh loan spell in March 2018. He signed permanently in the summer of 2018.