The striker has been the subject of two failed bids by the Blues, with Manchester United insisting it plans to keep hold of him, and the ex-player has warned against a switch.
The Premier League champion has already rejected two bids from Chelsea, the second of which was worth 30 million pounds, with Jose Mourinho keen to add the 27-year-old to his squad before the transfer window shuts.
Wilkins represented both clubs during his playing career but thinks Rooney would be making a mistake if he moves to Stamford Bridge and believes he should battle to establish himself under new Red Devils boss David Moyes.
“It shouldn’t end this way, it’s getting horrible,” Wilkins told talkSPORT. “I’ve said it in the past and I’ll say it again. Once you leave Manchester United there’s only one way you’re going.
“Man United are in the top three biggest clubs on the planet, therefore they will always buy and buy and buy, because they always want to be successful.
“If you want to win things then there’s no better club to be at than Manchester United.
“So what if you’ve got a bit of competition with Robin van Persie? It’s healthy. He should stand up to the plate and show these people what he's made of. He’s got so much wonderful football left in him."
Wilkins thinks Moyes should only consider selling Rooney if a foreign club makes an offer, although he has conceded he would love to see him play for Chelsea.
“If I was David Moyes there’s no way I would sell him to anyone in England,” Wilkins said. “I’m sorry – he’d have to go abroad.
“I would love him to join Chelsea though. I would love nothing more than to see Wayne Rooney wearing that blue shirt.
“I just think he’s ready for his second coming, he’s 27 years old and if for some strange outcome he stays in England, then Wayne is ready to start again.
“Man United would be crazy to do that though, they shouldn’t sell him to one of their closest rivals.”