Sol Campbell tasted defeat on his debut as a manager as Macclesfield Town were beaten by Newcastle United Under-23s in the EFL Trophy.
Scott Wilson had equalised just six minutes from time but the Silkmen went on to lose a penalty shootout for the first time in their 144-year history.
The former Tottenham, Arsenal and England defender was appointed as the Silkmen's new boss last week, with the club rooted to the bottom of the Football League.
Campbell was in the stands as Macclesfield earned a valuable win against Exeter last week but took charge for the first time on Tuesday evening.
Elias Sorensen poked home his 18th goal of the season in the 23rd minute but the visitors were on top for the majority of the first half.
Newcastle improved after the break, Sorensen missing a glorious one-on-one chance just a minute after the restart and again with 20 minutes to go, but found themselves pegged back.
With the Silkman pushing for an equaliser, it was Scott Wilson who popped up six minutes from normal time to chip Nathan Harker.
So it was to penalties and after the two teams scored their first spot kicks, Ben Stephens' effort was saved by Harker and the hosts saw out a 5-3 win in front of 1,126 fans.
