Town introduced all three recent new signings in ex-Sunderland pair Carlos Edwards and Grant Leadbitter along with Liam Rosenior from Reading whilst Middlesbrough welcomed the return of midfield player Gary O'Neil after a double hernia operation.
The home side took an early lead with a brilliant goal by O'Neil from right-wing cross by Marvin Emnes.. The 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
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 as the home side threatened to go into the interval with a two goal lead.
The half time team talk from Town boss Roy Keane appeared to fire up his side somewhat more, as they began the second half determined to pull the game round to get something from the match but Middlesbrough held firm.
There were some strong tackles flying around from both back lines with limited opportunities for the forwards to create openings or show their striking power.
Both managers introduced substitutes with Town boss Roy Keane bringing on Priskin, Quinn and Martin on for Counago, Delaney and Colback, whilst Gareth Southgates choice to bring on Jeremie Aliadiere proved a masterstroke.
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 to double the home sides lead.
Town rallied following the home sides second goal, and seemed determined to get a foot back in the game and the unfortunate McAuley saw another goal bound effort cleared off the line by Johnson.
Aliadiere increased the lead by grabbing his second and his sides third with just five minutes to go 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 who are still seeking their first win of the season in a campaign where they were expected to be amongst the promotion front runners.