Lands winning serves holding head of racket (5)
I believe the answer is:
acres
'lands' is the definition.
(thesaurus)
'winning serves holding head of racket' is the wordplay.
'winning serves' becomes 'aces' (I've seen this before).
'holding' is an insertion indicator.
'head of' suggests taking the first letters.
The initial letter of 'racket' is 'r'.
'aces' placed around 'r' is 'ACRES'.
(Other definitions for acres that I've seen before include "Cares about the tracts of land" , "farmland maybe?" , "Scare (anag)" , "Rival played" , "Extensive landed property (often rolling)" .)