The Huddersfield Town midfielder will face Boro tomorrow for the first time since leaving the Riverside at the end of June.
Beaten in the play-off final last term, Aitor Karanka’s men have made a positive start this time around and are one of five teams separated by just two points at the summit of the Championship.
This, though, is the least Whitehead believes should be expected of his former club having splashed £8m alone during the close season on former England internationals David Nugent and Stewart Downing. Karanka was also given the funds to bring in a host of high-profile loanees from the Premier League and abroad.
Whitehead, who spent two years at Boro, said: “Middlesbrough are a very strong side. Just like Derby, Burnley and Hull, they will be in and around the top two most of the year.
“They don’t concede many goals and spent so much money over the summer that they have loads of talent.
“I think they are under pressure to go up. This is a tough division and very demanding. But, from the moment they signed Downing, the thought was they would walk the league.
“The money they have spent and the squad they have got, it would be almost failure if they don’t go up.”
Tomorrow’s clash at the John Smith’s Stadium brings together two of the second tier’s four foreign managers as David Wagner hosts the Spaniard in what is the German’s home bow as head coach.
It promises to be a fascinating affair, as the majority of Town fans get their first glimpse of the ‘gegenpressing’ system that Wagner has imported to West Yorkshire from Borussia Dortmund.
Huddersfield impressed during the 44-year-old’s first game at Sheffield Wednesday before three goals in the final 12 minutes condemned the German’s side to a 3-1 defeat.
It meant the Terriers slipped a couple of places to fourth-bottom, but Wagner insists the prospect of dropping into the relegation zone come 5pm tomorrow is not even in his mind.
“In Germany, there is a sentence ‘Rome is not built in a day’,” said the Town chief. “This is good for us. We will build ourselves up much faster than Rome was built, though it will take time.
“But, if I am honest, I do not think about it (going into the bottom three). It is not interesting to me. Neither is who is the favourite to win the game or who is the underdog.
“This is a game against a very good team, but we will try to win. Hopefully, at the end, it will be enough to get a good result.
“To think about something negative is completely the wrong idea. I know we have enough quality to keep this game open. There will be some key moments and we have to win them.
“The table does matter because we are professional; no one wants to be at the bottom of the table. But we are realistic and we know we are in a good shape. We will get our results.”
Wagner yesterday made his second signing since succeeding Chris Powell as Aston Villa goalkeeper Jed Steer returned to the club until Boxing Day.
The 23-year-old made 10 appearances under Powell, but headed back to Villa Park after Joe Murphy was restored to the starting line-up.
Murphy is facing four weeks out after damaging his ankle in last weekend’s loss at Hillsborough.
As for whether Steer might extend his stay further after the festive season, Wagner said: “What I learned in football is not to look too far forward. Only look to the present or a few days in the future.
“The rest is too far away. We will discuss it later.”