Coventry are keen on the Dutchman, who was sacked by Queens Park Rangers last month.
Tony Mowbray resigned from the Sky Blues' post at the end of September with assistant Mark Venus filling in on a temporary basis.
Hasselbaink won only 13 of his 47 games in charge at Loftus Road but previously led Burton Albion to promotion from League Two and the top of the third tier before the R's came calling a year ago.
21st-place Coventry face a daunting visit from second-place Sheffield United on Thursday.
QPR meanwhile, appear to have taken Arsenal winger Tyrell Robinson on trial. The 19-year-old, who scored for the Hoops' Under-23s against Watford on Monday, spent time with West Bromwich Albion earlier in the campaign.
Hasselbaink's replacement Ian Holloway has so far not fared any better than his predecessor, losing three of his four games in charge.