Shrewsbury and Ipswich traded blows in a top-class Carling Cup tie of six high-quality goals before the Championship side won 4-2 on penalties.
Connor Wickham, only 16, scored with a crisp 18-yard right-foot drive for Ipswich after 11 minutes and then produced a dazzling display for the rest of the game.
Shrewsbury equalised with Jake Robinson's 12-yard snapshot before Dave Hibbert hit a stunning dipping 35-yard volley past Shane Supple.
Ipswich pulled level with an Alan Quinn 20-yard free kick after 32 minutes and then Ipswich went ahead again with more intricate footwork from Wickham who found the corner of the net with a left foot 12-yard shot.
Fifteen minutes from normal time, Shane Cansdell-Sherriff sent a left-foot volley on the turn in off the far post.
Substitute Omer Riza had a good chance to wrap up the tie in extra time for Shrewsbury but fired wide with only Supple to beat.
Supple saved Robinson's first penalty and Ipswich scored all four before Graham Coughlan fired the ball over the top to give Ipswich victory.
Teams
Shrewsbury Chris Neal, Holden, Coughlan, Langmead, McIntyre,Cansdell-Sherriff, Murray (Dunfield 106), Disley, Robinson,Elder (Bright 63), Hibbert (Riza 69).
Subs Not Used: Arestidou, Hooman, Gray, Simpson.
Booked: Coughlan.
Goals: Robinson 18, Hibbert 24, Cansdell-Sherriff 74.
Ipswich Supple, Ainsley (O'Connor 46), Bruce, Smith,David Wright, Colback, Healy, Garvan (Upson 46), Quinn,Lambe (Walters 78), Wickham.
Subs Not Used: McLoughlin, Brown, Murray, Hyam.
Goals: Wickham 11, Quinn 32, Wickham 59.
Ipswich win 4-2 on penalties
Att: 4,184
Ref: Mike Russell (Hertfordshire).