Tottenham will take on West Bromwich Albion at White Hart Lane in the Premier League on Monday evening.
Spurs will then face London rivals Chelsea away from home at Stamford Bridge in the league on Monday, May 2.
Former Arsenal striker Henry believes that the match against the Blues, who won the league title last season, will be key for Tottenham.
"For Tottenham the Chelsea game is key," the former France international striker told Sky Sports. "If they win at Stamford Bridge then it's game on, because I don't see them then losing other games. But Chelsea are going to try and play really hard against Tottenham.”
Tottenham should be able to win against West Brom at home, and the North London outfit will fancy their chances against Southampton at White Hart Lane and Newcastle United at St. James’ Park.
Chelsea are a very strong team - on paper at least - and they will make it very hard for Spurs. The Blues have performed better under manager Guus Hiddink, who will certainly want his players to give their all against London rivals Tottenham.