Roberts, now 65, made 278 appearances for Spurs between 1980 and 1986. He helped them win the FA Cup in 1981 and 1982, but he is most well-known for captaining Spurs to UEFA Cup glory in 1984.
With regular captain Steve Perryman suspended for the second leg in the final against Anderlecht, Roberts took the armband, scoring a late equaliser before converting his penalty in the shootout to guide Spurs to victory.
The six-time England international knows all about winning in N17, and he believes Spurs don't have enough leaders at the moment compared to the glory days of the 1980s under manager Keith Burkinshaw.
"We had so many leaders. [Glenn] Hoddle, [Steve] Perryman, [Chris] Hughton, [Tony] Galvin, Ossie [Ardiles], [Ricky] Villa, [Paul] Miller, and [Ray] Clemence. Not only were we a team of leaders, but we could all play and had character as well," he said.
"The game is short of characters, and Spurs especially lack characters and leaders on the pitch. This is so important as with different types of characters, especially those who need a lift during games; Spurs need to look at this in their next recruitment."
After a 1-0 defeat to Chelsea last night, Spurs now sit 14th in the Premier League. It is the first time they have lost 16 of their opening 30 league games since 1977, with the only hope of success this campaign now in the Europa League.
Next Thursday, Spurs host Frankfurt, who sit third in the Bundesliga, in the first leg of the Europa League quarter-finals. Roberts' greatest moment came in UEFA's second-tier competition, and he admitted that he always felt they could fight back despite going 1-0 down in the second leg of the final to Anderlecht.
"It was the best! To be named captain as Perryman was out was the greatest highlight of my career," he told the site.
"There was no added pressure, and I think I thrived being captain as i scored and also created the penalty we got in the final. We were 1-0 down, but I always felt our team could come back and win."