Ipswich Town came from two goals behind to beat Premier League outfit Wolves 3-2 in the third round of the Carabao Cup.
McKenna, who has developed a reputation as one of the brightest coaches in England after he masterminded the Tractors Boys’ promotion to the Sky Bet Championship last season, watched his team go 2-0 down early on.
Hwang Hee-Chan and Toti netted inside 15 minutes for the Premier League side but they still slumped to a fifth defeat in eight matches under new boss Gary O’Neil.
Omari Hutchinson started the Ipswich comeback with a fine 28th-minute finish before Freddie Ladapo ensured it was all square at half-time. Jack Taylor’s superb 25-yard strike soon after the break handed former Manchester United assistant McKenna his first victory over a top-flight club.
A total of 20 changes were made by both teams for this tie but it was Hwang, a starter for Wolves at Luton, who broke the deadlock in the fourth minute.
Ipswich’s Dominic Ball was at fault after he could only clear Pablo Sarabia’s cross to Sasa Kalajdzic, who passed through to the unmarked Hwang and the left-footed strike by the Wolves attacker was too powerful for Vaclav Hladky.
It silenced the expectant Portman Road crowd, which had seen the Tractor Boys making a flying start on their Championship return and win seven of their opening eight fixtures, but it was 2-0 after quarter of an hour.
Sarabia’s dangerous corner picked out full debutant Santiago Bueno and while Hladky made a fine save from point-blank range, Wolves defender Toti was on hand to smash home on the goal line to punish more slack Ipswich defending.
The narrative of McKenna’s all-conquering team being ready to claim a top flight scalp had not gone to plan so far, but the tide started to turn midway through the first half and Hutchinson reduced the deficit in the 28th minute.
The Chelsea loanee had looked a threat and when he was slipped in by Marcus Harness, he did not need a second invitation and rifled beyond Wolves captain Dan Bentley from eight yards with his weaker right foot.
It was Hutchinson’s stronger left foot which forced Bentley into action next but the visitors’ goalkeeper was able to tip over the 20-yard free-kick.
McKenna’s men were impressing now though and the equaliser arrived six minutes before half-time through Ladapo.
Ipswich’s reliable back-up forward was played in by Harness and his low strike was too strong for Bentley, who got a hand to the effort but failed to stop the hosts restoring parity.
A Harness shot deflected wide 50 seconds into the second period signalled the intentions of the Championship outfit and while Matt Doherty had a shot blocked for Wolves soon after, the fifth goal of the contest went to the hosts.
Harness again claimed the assist but it was all about former Peterborough midfielder Taylor, who received the ball around 25 yards out and let fly with a thunderous effort that flew past Bentley.
O’Neil reacted with Matheus Cunha introduced alongside forwards Fabio Silva and Nathan Fraser, but it was Ipswich’s night and a low save by Hladky from Bueno’s 73rd-minute header helped send McKenna’s side through to the last-16 of this competition for the first time since 2010.