Grassmoor, I've been trying to pinpoint the year{s} this was taken, I would take a stab at the seventies, possibly early seventies, can't narrow it down any further.
You are correct OC the road from the bottom is indeed Hagg hill from Tupton, the road that forks off left is Birkin lane west and when it reaches the main road {which runs right to left from North Wingfield towards Hasland and Chesterfield} the cars you can see parked on the left on the junction are parked were the old Roxy cinema once stood, these cars are part of the garage to the left of them, the garage "used" to be called Jack South's garage. The building on the right side opposite the cars is the Boot and Shoe {nicknamed the slipper}
The road opposite is Birkin lane which takes you to Temple Normanton. The first "field" to the left of it is Barnes park, the white dot near the trees in the park is the Cenotaph the estate on the opposite side of the park on Birkin lane is locally known as Southend.
The reason I think it's seventies. The smaller field behind the park is now an estate of houses {Durham avenue} these I believe have been up well over thirty years this is accessible of Norfolk avenue {to the left of the park} also the house opposite Norfolk avenue on the main road next door to Grassmoor primary school was built on the site of an old chapel which was demolished in the late sixties and I believe the house was then built between then and the early seventies.