A cutting head rotatable about a first axis in a direction of rotation, and comprising: an intermediate portion having an integer number N, N ≥ 2 circumferentially spaced apart peripheral surfaces, each peripheral surface having a leading edge, and the plurality of leading edges defining a cutting diameter; and a tip portion having an axially forwardmost tip point contained in the first axis and N front surfaces, each front surface having a radially extending front cutting edge which comprises an outer cutting edge extending radially inwardly from one of the leading edges and an inner cutting edge extending radially inwardly from said outer cutting edge, each inner cutting edge adjoining its associated outer cutting edge at a cutting edge transition point, wherein: in a cross-section taken in a first vertical plane parallel to the first axis and intersecting any one of the outer cutting edges, an outer rake surface adjacent to said outer cutting edge is inclined at a positive outer rake angle (α1); and in a cross-section taken in a second vertical plane parallel to the first axis and intersecting any one of the inner cutting edges, an inner rake surface adjacent to said inner cutting edge is inclined at a negative inner rake angle (α2), wherein: each outer rake surface is disposed on a head flute extending axially rearwardly from the tip portion and intersecting one of the leading edges; and each inner rake surface is disposed on a gash extending axially rearwardly from the tip portion and intersecting one of the head flutes, characterised in that each gash has a gash path defined by a plurality of gash apex points from a series of cross-sections taken in planes perpendicular to the first axis and intersecting the gash along its axial extent; each gash path extends to a gash path end point located a first distance axially rearward of the tip point; and the first distance is greater than thirty percent of the cutting diameter. an intermediate portion having an integer number N, N ≥ 2 circumferentially spaced apart peripheral surfaces, each peripheral surface having a leading edge, and the plurality of leading edges defining a cutting diameter; and a tip portion having an axially forwardmost tip point contained in the first axis and N front surfaces, each front surface having a radially extending front cutting edge which comprises an outer cutting edge extending radially inwardly from one of the leading edges and an inner cutting edge extending radially inwardly from said outer cutting edge, each inner cutting edge adjoining its associated outer cutting edge at a cutting edge transition point, wherein: in a cross-section taken in a first vertical plane parallel to the first axis and intersecting any one of the outer cutting edges, an outer rake surface adjacent to said outer cutting edge is inclined at a positive outer rake angle (α1); and in a cross-section taken in a second vertical plane parallel to the first axis and intersecting any one of the inner cutting edges, an inner rake surface adjacent to said inner cutting edge is inclined at a negative inner rake angle (α2), in a cross-section taken in a first vertical plane parallel to the first axis and intersecting any one of the outer cutting edges, an outer rake surface adjacent to said outer cutting edge is inclined at a positive outer rake angle (α1); and in a cross-section taken in a second vertical plane parallel to the first axis and intersecting any one of the inner cutting edges, an inner rake surface adjacent to said inner cutting edge is inclined at a negative inner rake angle (α2), wherein: each outer rake surface is disposed on a head flute extending axially rearwardly from the tip portion and intersecting one of the leading edges; and each inner rake surface is disposed on a gash extending axially rearwardly from the tip portion and intersecting one of the head flutes, each outer rake surface is disposed on a head flute extending axially rearwardly from the tip portion and intersecting one of the leading edges; and each inner rake surface is disposed on a gash extending axially rearwardly from the tip portion and intersecting one of the head flutes, characterised in that each gash has a gash path defined by a plurality of gash apex points from a series of cross-sections taken in planes perpendicular to the first axis and intersecting the gash along its axial extent; each gash path extends to a gash path end point located a first distance axially rearward of the tip point; and the first distance is greater than thirty percent of the cutting diameter. each gash has a gash path defined by a plurality of gash apex points from a series of cross-sections taken in planes perpendicular to the first axis and intersecting the gash along its axial extent; each gash path extends to a gash path end point located a first distance axially rearward of the tip point; and the first distance is greater than thirty percent of the cutting diameter.