In the run-up to the start of the 1999–2000 FA Premier League season, pundit Rodney Marsh predicted that Phillips would struggle to get more than five or six goals at the higher level. Forming a potent "little and large" strike pairing with veteran target-man Niall Quinn, Phillips scored his sixth goal on 18 September – the first of a hat-trick against Derby County – and was named Premier League Player of the Month for October. His goal tally was 20 by mid-January and 30 by the season's end, a total that earned him not only the Premier League Golden Boot but also the European Golden Shoe award – , he remains the only Englishman to have won the latter – and with a 14-goal return from Quinn contributed to Sunderland's seventh-place finish, just missing out on a UEFA Cup place.