Charlie Pye, from Leamington Spa, applied for the Villa hotseat after Paul Lambert was sacked in February
The Villa fan wanted a chocolate bar as a win bonus and would have agreed terms for a signed claret and blue football, a WWE wrestling figure and some sweets.
Sherwood wrote Charlie a letter congratulating him on his credentials, despite missing out on the job.
He wrote: "From your letter it is clear to see that you would indeed be an ideal candidate for the job due to your knowledge of the game - and your very capable backroom staff, of course!
"Hopefully you're not too disappointed at missing out and I'm informed that I just managed to pip you to the post so you were very close to being offered the job.
"Our chief executive Tom Fox has informed me that the club would like your permission to keep the letter on file 'just in case' - although I'm hoping I will be successful at this great football club.
"I will certainly be aiming to make you and all the other supporters happy.
"In terms of your football career, I want to wish Norton Lindsey every success this season
Well done on being appointed captain
I was a captain during my own playing career - it's a special honour."
Sherwood has guided Villa six points above the relegation zone in the Barclays Premier League after Saturday's 1-0 win at former club Tottenham and taken them to Sunday's FA Cup semi-final against Liverpool
Charlie had written to chief executive Tom Fox after Lambert was sacked with Villa in the relegation zone earlier this year.
He wrote: "I would appoint my mum and dad as assistant managers so they can drive me to the training ground each day
My mum is also very good at making bacon sandwiches for the players if that helps."
Charlie told the club's official site: "I never expected a letter from the manager but I was absolutely delighted to get one
"What he wrote was brilliant - it meant a lot to me
Even the stuff about congratulating me on being a captain was really special."
Source : PA
Source: PA