Maidenhead United are set to hold a testimonial for club captain Alan Massey who is set to leave the club this summer after making 384 first team starts for the Magpies over the course of the past 10 years.
Massey’s arrival at York Road heralded the club’s greatest period of success, with the Magpies earning promotion from the National League South and spending the past eight seasons competing at the top level of non-league football.
Manager Alan Devonshire made Massey one of his first signings after joining the club for a second spell as manager in the summer of 2015, and he would arguably be his most important signing of the past 10 years, the standard setter for progress and improvement that was to come.
The former Wycombe Wanderers and Wealdstone man followed Devonshire to York Road from Braintree Town, initially dropping down a division to join the Magpies from the Iron.
He immediately slotted into the heart of a new-look defence, with assistant manager Ryan Peters playing alongside him at right back. They made a serious push for the play-offs in Devonshire’s first season in charge and a memorable run to the first round of the FA Cup reached its peak when Massey fired Maidenhead ahead in their first-round replay against League 1 Port Vale at York Road.
His crisply struck effort from the edge of the 18-yard-box is fondly remembered by Maidenhead fans in a match that was broadcast on television. Vale would respond and win the replay 3-1, but Massey’s status as a fans’ favourite had been firmly sealed.
The club’s play-off push ran out of steam in the final weeks of the season, but Devonshire then put the final pieces of the jigsaw together for promotion the following season, with Massey replacing the departing Mark Nisbet as club captain - a crown he has worn with distinction for nine consecutive seasons.
Fittingly, the new skipper started all 42 National League South games as United racked up 98 points to win the title.
Massey’s trademark sense of humour – and the club’s underdog spirit - was demonstrated best after they sealed the title on the final day at Margate.
The captain lifted an inflatable trophy donated by delirious pitch invading fancy-dress wearing fans, with the National League powers-that-be having sent the silverware to Ebbsfleet United, banking on a Maidenhead slip-up that never materialised - the Magpies claiming a comfortable 3-0 win.
Your semi-regular reminder that, on the final day of the 2016/17 season, with Maidenhead United top of the Conference South table, League officials sent the trophy to 2nd-placed Ebbsfleet. We duly thumped Margate, and Alan Massey held aloft an inflatable (brought along by a fan). https://t.co/dkPf5WXvNd pic.twitter.com/Tlug8vXN6k
— ɢᴏ ᴍᴀᴅ ᴏʀ sᴛᴏᴘ ᴄᴀʀɪɴɢ (@gomadstopcaring) April 25, 2025
Over the past eight seasons in the National League, Massey has been a reassuring presence at the back, playing with distinction whenever he was called upon.
A tree surgeon by trade, he and Maidenhead confounded critics and expectations to maintain their place at the highest level of the non-league pyramid.
Massey’s 384 first team starts – in addition to being named as a substitute 74 times – make him the fourth highest appearance maker in Maidenhead United history, behind fellow greats Brian Pitts, Derek Randall and Michael Chatterton.
He managed only four first team goals across his decade playing for the Magpies. However, supporters never held this lack of goal-scoring prowess against him
Massey has also proved himself a true ‘club man’, attending community events on behalf of the club and regularly joining supporters for a post-match pint in Stripes Sports Bar, whatever the result.
A statement from the club today said: “All at Maidenhead United wish Alan Massey the very best for the next phase of his career.
"It is a case of ‘farewell’ and not ‘goodbye’ as Alan will return to the club very soon for a testimonial match to give our supporters the opportunity to share their best wishes with one of the all-time MUFC greats and to celebrate his many achievements.
“Watch out for further details of this event over the coming weeks.”
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