Harry Kane's brilliant improvised finish saw Spurs head into half-time with the advantage on Saturday but a spirited Leicester, who had seen an Ayoze Perez goal chalked off early on, fought back following the interval.
After a Serge Aurier strike had been ruled out by VAR due to the tightest of offside decisions, Ricardo Pereira got the Foxes back on level terms when he arrived to convert Jamie Vardy's low cross.
Leicester's comeback was then crowned when the impressive Maddison struck from distance five minutes from time.
The result means Tottenham have still not won an away game in the Premier League since January, while Leicester climb above them into the top four.
🔥 JAMES MADDISON 🔥 pic.twitter.com/h5TprN3iks— NBC Sports Soccer (@NBCSportsSoccer) September 21, 2019