Casey Pettit fired the hosts in front after 14 minutes, Callum Cooke struck back with a perfectly timed volley six minutes into the second half, but Sam Beckwith and substitute Shawn McCoulsky secured victory for Alan Devonshire’s determined Maidenhead with two goals in the final quarter-of-an-hour.
Here are five moments you might have missed from a disappointing evening for Pools:
1. A terrible record on Tuesdays
Pools have only won twice when playing on a Tuesday all season, losing their last two midweek matches by an aggregate score of 10-2. Kevin Phillips believes the midweek malaise is evidence that his side aren't fit enough. Photo: Mark Fletcher
2. Pools fail to produce a timeless performance at historic York Road
Supporters who made the long trip to Berkshire might have noticed the old school feel of York Road, which has been Maidenhead's home since 1871. FIFA and the FA recognise the ground as the oldest continuously used senior association football ground in the world. Photo: FRANK REID
3. Phillips pits his wits against veteran manager Alan Devonshire
Tuesday night's win means it's almost certain that Alan Devonshire has kept part-time Maidenhead in the National League for another season. Devonshire, who like Phillips won eight England caps during a distinguished playing career, first took charge of the Magpies in 1996 and has been at the helm for a total of 18 years. The 67-year-old took over less than a year after Phillips made his debut for Sunderland. Photo: Mark Fletcher
4. Agyemang gets a go in midfield
Middlesbrough loanee Terrell Agyemang was handed a rare opportunity in his professed preferred position of central-midfield when he replaced Chay Cooper midway through the second half, with the 21-year-old showing a few moments of promise in the middle. Photo: Frank Reid