Sherwood was wanted by Gunners manager at the time Bruce Rioch, though the deal fell through when Rioch was sacked.
"I was days away from becoming an Arsenal player in the summer of 1996," he wrote in his column for The Independent.
"When Bruce Rioch called me at home on an August night, I expected him to tell me what time to get to London Colney for my medical. Instead he told me he'd been sacked and the deal was off. They ended up signing some lad called Patrick Vieira. Three years later I joined Tottenham Hotspur and went back to my North London roots.
"To my mind, there was nothing like the north London derby. They were the most intense games I played in. When I scored the second goal from a free kick at White Hart Lane in a 2-1 win over Arsenal in November of my first full season, the place shook. It was electrifying."
The 44-year-old spent four years as a player at White Hart Lane and scored 12 goals during his time at the club.