Play again on middle of March and middle of June (5)
I believe the answer is:
rerun
'play again' is the definition.
('run' can be a synonym for 'play' so perhaps 'rerun' is OK for 'play again')
'on middle of march and middle of june' is the wordplay.
'on' becomes 're' ('on' can be mean 'with reference to'**).
'middle of' means to look at the middle letters.
'and' says to put letters next to each other.
'middle of' says to take the centre.
The middle letter of 'march' is 'r'.
The middle of 'june' is 'un'.
're'+'r'+'un'='RERUN'
(Other definitions for rerun that I've seen before include "Repeat showing of film or TV programmed" , "Show (eg, film) again" , "Film or programme broadcast again" , "Second broadcast" , "return to track" .)