After expressing his desire to be loaned out in determination of making a breakthrough at Sheffield Wednesday, Dieseruvwe joined Chesterfield on 3 January 2015 on a youth loan deal. Upon moving to Chesterfield, Dieseruvwe described the move as "a big chance" and "another step up". On 17 January 2015, Dieseruvwe made his Chesterfield debut, in a 3–1 loss against Swindon Town. Soon after, Dieseruvwe told of being settled at Chesterfield.
