Whichelow made his Championship debut for Watford against Scunthorpe United in October 2010 coming on as substitute.
Days later after making his professional debut, he again came on as a sub at Half Time at Derby County’s Pride Park and within 10 minutes scored his first professional goal. He went on to feature for Watford 17 more times that season, which included 4 starts and 2 goals.
Having missed most of pre-season in 2011/12, Whichelow joined Exeter City on a month’s loan to gain match fitness. After returning to Watford he came on as a substitute in the second half against Tottenham Hotspur in the FA Cup impressing many.
Matty was then loaned out to Wycombe Wanderers on another one-month loan deal. Following his Loan spell with Wycombe he gained more league experience with Accrington Stanley in division two with a 3 month loan at the Lancashire club. However upon his return to Vicarage Road and with Watford heavily taken with loan signings blocking his way to the first team, he was released by mutual consent.
On the arrival of Whichelow Ian Allinson said ” Matty is a young player I’ve liked for a long time and seen him develop well at Watford. Like many of Watford’s young players before him like Chez Isaac and Piero Mingoia, when I’ve seen their availability I’ve tried to sign them. I think if Matty can believe in himself and his ability like I do, if he works hard out of possession as well as in possession then he’ll improve very quickly. Firstly though we must get him enjoying his football again and when we do he’ll be an asset to ourselves and to our ambitions and we can then help him get back into the league, so I hope it’s a perfect fit, we’ll see.” He concluded..