Hasselbaink served both clubs with distinction during his playing career.
He said: "For Leeds, obviously, to be able to play in a quarter-final of the Capital One Cup is absolutely magnificent.
"They will have a good chance of going through to the semi-finals.
"They have seen Bradford doing it so I think they will take great inspiration from that and will be looking forward to the game. The game can't come quick enough for them.
"If I was Chelsea's manager, I would want to have a few more days to prepare for this match.
"They will have to go through it and hope they turn up and do not feel too tired.
"The odds are getting better and better for Leeds."