Headland made a bright start to Saturday night’s three-point loss to Richmond, booting two goals and taking a spectacular mark before injury struck just before half time.
Headland and Michael Johnson (ankle) both had scans on Sunday and the results will be discussed at a planning meeting late on Monday.
The club remains hopeful that Johnson and Luke McPharlin (hip) will be available for the AAMI Stadium clash with Port.
Draftees Stephen Hill (cork) is unlikely to play this week.
With Hill, Headland and McPharlin all unable to return to the field in Saturday night’s loss, Fremantle was forced to play the second half with 19 fit men.
However, Paul Hasleby (calf), Antoni Grover (shoulder) and Byron Schammer (groin) were all carrying injuries.
All three will be monitored this week, but the club is confident they will be available.
The versatile Kepler Bradley, speedster Clayton Hinkley and rookie Clancee Pearce are all possible inclusions this week to cover injury, while Fremantle coach Mark Harvey suggested Ryan Murphy, Daniel Gilmore and Adam Campbell may be pulled out of Monday’s Foundation Day WAFL fixtures.