Despite Arteta having Arsenal clear at the top of the Premier League table and in a good position in the Champions League quarterfinals, Hasselbaink says the Basque is lucky to be in the job.
He told Sky Sports: "Arsenal are in a great position at the moment, but let's not forget how long he's been there.
"He has won one FA Cup. For a club like Arsenal, is that enough?
"Yes they are in a really good position, but let's how a look how much he has spent in the last two years - a lot of money. He has got two good squads, the bench is really strong. Should they not be more ahead?"
Hasselbaink added: "You look at the football - they are pragmatic,. They are solid they don't give a lot away.
"Yes, that's how you win the league normally. Would I want to see more the Arsenal way? Yes. With a bit more flair. But that is me, a lover of football."