A surgical stapling head assembly with a rotary cutter comprises a casing (101), an annular cutter (103), a staple driver (102) and a staple holder. Said staple driver (102) is connected with the annular cutter (103) by a bearing structure (109) with guiding projections (115a, 115b, 115c) disposed thereon, on the outer wall of the anti-expansion tube (104) or the inner wall of the casing (101) is molded with a metal cylinder member (105), on which is provided with a forward helix track (106) and a backward track (107) independent and communicated with each other, the guiding projections (115a, 115b, 115c) engaging with the two guiding tracks (106, 107) to guide the annular cutter (103) to forward in way of helix.