Sheringham fears for the club as they prepare to face Spurs, another of his old teams, in tomorrow's crunch Premier League teatime clash.
He told The Sun: “Maguire is having a ragged time. Once they went 2-0 down, the game plan and cohesion went out of the window, people started doing their own thing and it became chaos. Everyone was at sixes and sevens.
“That's where you need to keep your head and you need a good skipper who tells everyone, 'Calm down, we'll get back into it'.
“It doesn't look like there is a proper captain out there leading and demanding they stay in their structure."
According to Sheringham, Maguire could take a leaf out of former teammate Steve Bruce's leadership book.
He said: “When you keep conceding goals, you need a big, strong leader and defender.
“When United started their good reign, Steve Bruce and Gary Pallister tucked their full-backs in and told them they go nowhere.
“They didn't care how many crosses a young Gary Neville and Denis Irwin put in as long as the opposition didn't put any in, they stayed tight and didn't concede. A top player would win it at the other end.
“It seems like everyone is doing their own thing and looking after themselves — and that's not how a team works.
“They need to stand by each others' sides, dig deep in the trenches and work hard together to pull through."