Windass, 40, has decided to hang up his boots after an 18-year playing career in order to focus on completing his UEFA coaching badges.
Windass, whose winning goal in the play-off final against Bristol City in 2008 lifted hometown club Hull into the Premier League for the first time, said: "It has always been my intention to get into coaching and management and while I understood how difficult that maybe, I was happy to get some experience at the earliest opportunity at Darlington working under someone as knowledgeable as Colin Todd.
"I was also happy to continue playing and combine our tactical aims with the added impetus of being on the pitch.
"As far as playing is concerned you are a long time retired, but I can honestly say now that I want to channel all my enthusiasm into coaching and ultimately management."
Windass, who also played for Oxford and Sheffield United, played his last league game as player/coach for Darlington in their 2-0 home defeat by Bournemouth in September.
He and Todd were sacked and replaced by Steve Staunton and Kevin Richardson shortly after.