The 24-year-old defender, who made a solitary League Cup appearance for United in 2009 before joining Hull a year later, pounced to put Hull in front after four minutes but his Christmas turned sour when he later headed into his own net.
Even then his day could have had a fairytale ending but his stoppage-time shot was saved by David de Gea when he had looked poised to equalise.
"He put one in his own net. We've all done it and he'll have to live with that but he'll get over it because he's a very good young player."
When Chester scored and David Meyler made it 2-0 it looked as though Bruce, who is yet to taste victory against his old club as a manager, would finally get one over the Old Trafford side.
However, quickfire goals from Chris Smalling and Wayne Rooney levelled it up before halftime and Chester's own goal on 66 minutes sealed victory for United.
"Over the years I've been close a few times to beating them but never 2-0 up against them within 15 minutes and the one thing we've been able to do since I've been here is hold a lead," Bruce said.
"We made too many mistakes at crucial times. We created umpteen opportunities in the second half but we made mistakes and you get punished against a team like Manchester United."
- Sports & Recreation
- Manchester United
- James Chester
- Steve Bruce
- David de Gea