Town's U16s drew 3-3 with Manchester United in an entertaining friendly at Portman Road on Friday evening, but lost a penalty shoot-out 5-3 to the Premier League club's academy side.
The young Blues went in front with less than five minutes on the clock, Cormack Burke crossing from the left and United keeper Sam Johnstone palming the ball out to Connor Wickham, who tapped home.
The visitors hit back almost immediately with Norwegian youth international Joshua King beating stand-in Town keeper Kai Hewitt.
The Blues were due to field a Norwegian of their own between the sticks but Alex Stensrud, who joins the academy full-time in the summer, injured his thumb in training and was in plaster and unable to play. TWTD first reported Town's interest in Stensrud back in 2006 when he came to Playford Road for a trial as a 14-year-old.
Irish U16 international Ronan Murray was the most impressive player in the first half before being replaced at the break and the striker put the Blues back in front on 18, cutting in from the left and lashing a shot across the keeper and into the net.
Town had been the stronger side in the first period, but United improved after the break, pinning the Blues back in their own half for the most part.
However, before they could make their pressure tell, midfielder Billy Clark, another of this summer's full-time intake, netted the goal of the night in the 49th minute to increase Town's lead, hammering in a 30-yard screamer which gave Johnstone no chance.
United eventually pulled a goal back in the 58th minute through sub William Keane and the same player put the Red Devils on terms on 70. The visitors had more than a few chances to grab a win with the Town goal leading a charmed life in the final few minutes.
The draw was probably a fair result, but United eventually grabbed the win via spotkicks 5-3, Town's Josh Meekings the unlucky man.
Town: Kai Hewitt, Sam Brandon, Derek Williams, Josh Meekings, Tom Eastman, David Cawley, Cormac Burke, Billy Clark, Connor Wickham, Ronan Murray, Seb Dunbar. Subs (all used except De Laraball): Jamie Griffiths, Max Westcott, Billy Shulver, Nathan Ralph, Josh Capocci, Charles De Laraball.
Shoot-out: Manchester United: William Keane (scored), Larnell Cole (scored), Johnny Gorman (scored), Ryan Tunnicliffe (scored) and Robert Brady (scored).
Ipswich Town: Billy Clark (scored), David Cawley (scored), Ronan Murray (scored), Josh Meekings (saved) and Connor Wickham (did not take).