Running on soft ground she took the lead at half way and won by twelve lengths from College Music despite being eased down by Charnock in the final strides.
[9] Kieren Fallon took the ride when Pipalong moved up in class to contest the Group Three Queen Mary Stakes at Royal Ascot in June.
Charnock resumed the mount in the six furlong Cherry Hinton Stakes at Newmarket Racecourse in July in which the filly set the early pace before finishing second of the ten runners behind Wannabe Grand.
After a break of almost three months, Pipalong returned in the Oh So Sharp Stakes over seven furlongs at Newmarket and finished fourth behind Snittersby, Fragrant Oasis and Hula Angel (later to win the Irish 1000 Guineas).
On 17 October Pipalong started 5/2 favourite in a 22-runner field for the Listed Comcast Teesside Two-Year-Old Trophy over six furlongs on heavy ground at Redcar Racecourse.
She was among the leaders from the start, went to the front in the last quarter mile, and rallied after being headed by the colt Pistachio to regain the lead in the closing stages to win by a neck.
On 14 August at Ripon on soft ground the filly was matched against colts and older horses in the Great St Wilfrid Handicap and was assigned a weight of 131 pounds in a 23-runner field.
On her seasonal debut she started odds-on favourite for a minor race over six furlongs at Thirsk and won by three and a half lengths from her stablemate Hot Tin Roof.
In the Listed Cecil Frail Stakes, for fillies and mares at Haydock on 10 June, Pipalong started odds-on favourite against five younger opponents.
[16] Racing on firm ground at Royal Ascot, Pipalong made little impact in the Cork and Orrery Stakes, finishing unplaced behind Superior Premium.
In the Group One July Cup on good-to-soft ground at Newmarket she produced a much better performance as she was narrowly beaten in a three-way photo finish by the Japanese colt Agnes World and the three-year-old Lincoln Dancer with Primo Valentino and Lend A Hand in fourth and fifth.
The six-furlong Stanley Leisure Sprint Cup at Haydock on 6 September saw Pipalong start the 3/1 second favourite behind Lincoln Dancer for a race run on heavy ground.
[18] On her final appearance of the season, Pipalong was sent to France for the Prix de l'Abbaye over 1000 metres at Longchamp Racecourse in October and finished third behind Namid and Superstar Leo.
In March 2001 Pipalong was sent to the United Arab Emirates for the Dubai Golden Shaheen but finished tenth of the fifteen runners behind the American gelding Caller One.
Bertolini started favourite ahead of Astonished with Bahamian Pirate, Vision of Night and Hot Tin Roof also among the fourteen-runner field.
The mare produced what was described as a "cracking effort",[19] taking the lead approaching the final furlong and holding off the sustained challenge of Tedburrow to win by a neck.