About 165 people braved the cold and slept out at Wolverhampton Wanderer's Molineux Stadium on Friday.
Organised by the Wolves Foundation, the sleepout has so far raised over £30,000 for rough sleepers in the city.
Carl Ikeme, former Wolves goalkeeper and ambassador for the charity Good Shepard, was there alongside grime and rap artist Reepa.
Mr Ikeme said the sleepout was to show "solidarity, support and awareness" of homelessness.
"I remember visiting the Good Sheppard about 10 years ago and I was surprised by how many people used them," Mr Ikeme added.
The money raised will go to Good Sheppard and the Wolves Foundation.
"Wolves is an amazing community and they do come together for these sorts of causes," Mr Ikeme said.
Reepa, from the Heath Town area of the city, said the exposure the football club offers will hopefully help raise more awareness of the issue.
"As well as raising money it is awareness, I think awareness is more valuable than the money," he said.
"This is Wolverhampton Wanderers football club, the biggest platform the city has to offer.
"The exposure that we can offer and the awareness that we can raise... is second to none."
Organiser Will Clowes said while the sleepout has an element of fun about it, it is also "the realisation that sleeping outside is difficult and challenging".
Mr Clowes said he hopes the final total raised will be £50,000.
Mayor of Wolverhampton Dr Michael Hardacre said it is "one of the most important nights of the year".
He said that "271,000 people in England are homeless one way or another, that is actually equivalent to the whole population of Wolverhampton".
Dr Hardacre said while "we have virtually elimination it in Wolverhampton", more needs to be done.