Manager Gareth Southgate must be pleased at the way that his relegated side has responded to the Championship challenge, but Roy Keane obviously has his work cut out at Ipswich.
Ipswich have yet to win a game and have only two points to show from six matches.
Middlesbrough welcomed the return of midfield player Gary O'Neil after a double hernia operation.
Ipswich introduced three new signings in ex-Sunderland pair Carlos Edwards and Grant Leadbitter along with Liam Rosenior from Reading.
Middlesbrough took an early lead with a brilliant goal by O'Neil from right-wing cross by Marvin Emnes.
O'Neil, a former Portsmouth player, picked himself up off the deck after appealing in vain for a penalty and scored with a header just under the bar.
Ipswich hit back and skipper David Wheater cleared off the line from Gareth McAuley.
It was a lucky escape for Middlesbrough but they deserved to be ahead in an opening half-hour in which neither goalkeeper was under a great deal of pressure. First-time tackling restricted opportunities for the forwards
O'Neil received treatment after a Leadbitter challenge which earned a strong word from the referee.
Middlesbrough were struck a blow close on the interval when defender Andrew Taylor collapsed near the touchline.
It was obvious that Taylor had suffered a serious injury and it was no surprise when he was carried off on a stretcher.
Close on half-time, Ipswich goalkeeper Richard Wright brought off a brilliant save from a Adam Johnson piledriver.
Ipswich began the second half determined to pull the game round but Middlesbrough held firm.
There were some strong tackles flying around with limited opportunities for the forwards to create openings or show their striking power.
Both managers introduced substitutes with an inspired choice by Southgate in Jeremie Aliadiere.
The former Arsenal player had only been on the pitch for a few minutes when he flicked a near-post header from a Johnson left-wing cross into the net.
Ipswich hit back and the unfortunate McAuley saw another goal bound effort cleared off the line by Johnson.
Aliadiere increased the lead and Middlesbrough looked set for another clean sheet until Ipswich grabbed a 94th minute penalty through Jon Walters.
Keane will need all his experience and motivation to transform the fortunes of his second bottom of the table side.