Port Vale were in outstanding form during the 1998-99 season, they finished the season off winning a staggering 31 matches and gained a total of 101 points, Keegan proving to work wonders at the club. They won the division title with three weeks to spare, in turn promoting the club to the first division. Port Vale put on a decent run in the league cup, crashing out against Liverpool in the third round, losing 3-1. They also put on a great run in the FA Cup, reaching the fifth round, only losing out to the eventual winners, Manchester United, 1-0.
The 1999-2000 season saw Port Vale put on a strong show in the first division, they narrowly missed out on a play off birth, finishing the campaign off in ninth position. The Cottagers embarked on their finest league cup campaign in years as they reached the last eight, they lost out on penalties against Leicester City, after a thrilling 3-3 draw. Port Vale reached the last sixteen of the FA Cup for the second successive season, losing 2-1 against Tranmere Rovers.
The 2000-01 season was the second time that Port Vale tallied more than 100 points by the end of the season. They embarked on an incredible run in the first division, finishing the season once again with 101 points, this time promoting the club to the premiership. Their new rising star, Louis Saha was in inspirational form through out the season. They once again reached the quarter finals of the league cup and they agonizingly lost 3-0 against Liverpool. The main down point of the 2000-01 campaign was the injury suffered to Chris Coleman in a car crash, in turn breaking his leg and later on resulting in retiring from playing professional football.
 Port Vale put on a good show during their first season back in the top flight for 34 years, they finished the season off in a comfortable 13th position, establishing themselves on the premiership map. The 2001-02 season also saw Port Vale embark on a fantastic run in the FA Cup, they eventually lost against Chelsea in the Semi finals, 2-1.