Tamas Priskin's goal gave Ipswich the first-leg advantage, holding off a defender before sliding the ball past goalkeeper Wojciech Szczesny in the 78th minute.
Kenny Dalglish's first Premier League match back as Liverpool manager ended in the club's second loss this season to Blackpool, which returned to the top flight after a 39-year absence.
Fernando Torres scored after three minutes, but Blackpool's Gary Taylor-Fletcher leveled nine minutes later and teammate D.J. Campbell's second-half goal inflicted Liverpool's 10th loss of the season.
Ipswich has had a turbulent week with Roy Keane leaving as manager and Paul Jewell appointed as his successor. The team is only three points above the League Championship relegation zone, and had been thrashed 7-0 at Chelsea in the FA Cup on Saturday.
"Pretty much everyone in the country wrote us off today, so we've surprised a lot of people," Ipswich captain David Norris said. "We let a lot of people down against Chelsea. We didn't do ourselves justice, so we went out tonight with that bit of extra determination and did what we had to.
"But there's still work to be done and we still have to go to the Emirates in the second leg."
Looking for his first trophy since the 2005 FA Cup, Arsenal manager Arsene Wenger fielded strong side that included Spain World Cup winner Cesc Fabregas and England internationals Theo Walcott and Jack Wilshere.
But the Premier League's third-place team failed to hit top gear and was fortunate not to lose by a bigger margin ahead of the second leg on Jan. 25 at Emirates Stadium.
"We didn't create many chances," Wenger said. "Ipswich defended very well and we were caught out. We had no spark. Ipswich were sharper than us and we made a defensive mistake, which they took advantage of. But we're at home in the second leg and that could make all the difference."
Blackpool showed that the 2-1 result at Anfield in October was no fluke and exposed the size of the task facing Dalglish, who returned Saturday to the job he relinquished 20 years ago following Roy Hodgson's dismissal.
Dalglish's challenge is not to deliver Liverpool's first English league title since 1990, but to keep the 18-time champions in the top flight. They are four points above the drop zone with 17 matches to go.
It began well for Liverpool. Dirk Kuyt passed the ball to Martin Kelly, who advanced over the halfway line before rolling a pass into the inside-right channel. Torres raced into the penalty area and sent a fierce shot past goalkeeper Richard Kingson into the roof of the net from a tight angle.
It was the Spain striker's second goal in his last nine matches, and seventh of the season.
But the visitors' joy lasted only until the 12th minute. Liverpool midfielder Raul Meireles carelessly gave the ball away in midfield to David Vaughan, whose pass allowed Taylor-Fletcher to run through the defense before rolling a shot under goalkeeper Pepe Reina.
Blackpool's winner came in the 69th, Ian Evatt beating Liverpool defender Martin Skrtel to Neal Eardley's deep cross for Campbell to head home.
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