Hay was awarded the prestigious Perth Glory Most Glorious Player award. The following season proved to be more successful for Perth Glory finishing 3rd after losing the preliminary final to Sydney United at Sydney on 23 May 1999. Hay was awarded again the prestigious Perth Glory Most Glorious Player award this time jointly with Scott Miller. Leeds United In June 1999, Hay trialled for Bundesliga side VfB Stuttgart before trialling the following month for FA Premier League side, Leeds United on the first team's pre season tour of Sweden and Finland. On 14 July 1999, Hay started in their friendly match against Swedish side Byske IF. On 17 July 1999, he started again and played the full fixture against Finnish side Tervaritahdet in Oulu. Hay was rested for the final match against Swedish side Bodens BK. Due to trial commitments Hay was unavailable for international duties at the Confederations Cup in Mexico. Hay was successful in obtaining a three-year contract with Leeds and became the first New Zealander to be offered a contract by a Premier League club. Hay was initially included in Leeds' Reserve squad for the 1999—2000 Premier Reserve League season where he started in the majority of the 24 fixtures between August 1999 and May 2000. Hay's time at Leeds was marked by injuries and all his appearances for the club's first team featured in less than a two-month period from when he debuted for the team in the UEFA Champions League. His time with the team was mainly on the bench when the team itself was ravaged by injuries. On 30 September 1999, Hay was named on the bench for Leeds' second leg UEFA Cup first round fixture against Partizan Belgrade at Elland Road. UEFA Champions League On 13 September 2000, Hay was named on the bench for their UEFA Champions League first group stage fixture against FC Barcelona at the Nou Camp. Hay came on in the 89th minute as a substitute for captain Lucas Radebe who suffered what appeared to be a serious neck injury. Hay's appearance as a replacement albeit brief was the first appearance by a New Zealander in the UEFA Champions League since Oceania Footballer of the Century, New Zealand International and Werder Bremen striker, Wynton Rufer. After making an appearance in the game against Barcelona, Hay was named on the bench but didn't see the field again for Leeds in