AFC Sudbury fielded what was believed to be the youngest side in the club's history at Bostik League Division One North leaders Canvey Island, but were only denied a point after a controversial 10th minute stoppage-time penalty went against them.
Captain Sam Clarke failed a late fitness test, meaning teenager Alfie Carroll was brought in to play centre-half alongside Will Crissell, last season's Suffolk Under-18s captain and new signing from manager Mark Morsley's old club Needham Market.
It meant the oldest player on the visitor's end of the pitch at last season's fellow Isthmian League Premier Division relegated side was 26-year-old goalkeeper Paul Walker.
Canvey controversially took the lead from their first attack in the eighth minute when George Craddock's strike was adjudged to have crossed the line.
AFC hit back within 10 minutes though with Carroll heading home when unmarked, but Canvey regained the lead before the interval through Ryan Charles.
Young Ollie Peters' stunning lobbed effort looked to have secured a point in the final minute of normal time, but after 10 added minutes, following eight being signalled, AFC conceded a penalty from which Mitchell Gilbey secured all three points.
Though disappointed not to get a result, manager Mark Morsley was delighted with the performance from his young side.
"We were cruelly denied at the last but we are not going to concentrate on that. What we are going to concentrate on is the second half performance," he told the AFC Sudbury Twitter account.
"It was really difficult conditions. To be 2-1 down at half-time to come out in the second half and and put in that performance was absolutely outstanding. There were so many plus points and so many good performances."
Reflecting on picking what is thought to be the club's youngest ever 11, he said: "It is great for the future of the club but I am not just doing that to try and get the records, I am doing it because these boys are good enough. Against a side that are top of the league these lads got the ball down and played some really good football in such tough conditions.
"I am just gutted for them they didn't get the point they deserved."
The result saw AFC drop two places to 16th in the table, though they do hold games in hand against the side around them.
Elsewhere in the division, former Sudbury left-back Jack Wilkinson made his debut for Mildenhall Town as they lost 2-0 at home to Heybridge Swifts, who scored in the second and 65th minutes in front of a crowd of 228 to leave Hall 13th.
Bury Town won 2-1 at Romford despite playing an hour with 10 men, following Darren Mill's first-half dismissal.
Tevan Allen marked his return to the club from AFC Sudbury by scoring an injury-time winner for Ben Chenery's side, who had gone behind to Craig Jeakins' 50th minute opener before Ollie Hughes levelled the scoreline 11 minutes from time.
The result means Bury remain in sixth place in the table.
Soham Town Rangers are 18th in the latest standings after a 2-1 defeat at home to third-place AFC Hornchurch, with The Greens' only goal seeing Lee Chaffey reply to George Purcell's opener just after the re-start, before Purcell hit what was to be the winner just after the hour-mark.
In the Bostik League Premier Division, Needham Market lie in 20th place, following a 3-2 loss at Dorking Wanderers.
Lewis Taylor fired the hosts in front in the 18th minute, which is how it remained at half-time.
But after Jamie Griffiths levelled things up six minutes after the restart, James McShane soon made it 3-1, before Griffiths pulled another back, which only proved to be a consolation strike, in the 75th minute.
In the Buildbase FA Vase First Round, Debenham LC will have another chance to equal their longest run in the national competition after today's tie at higher-league Thetford Town ended in a 1-1 draw.
Tanner Call sent Thetford into the break with a 1-0 advantage before Lamell Howell's spectacular effort just past the hour mark levelled things up, with extra-time not able to yield a winner, meaning the sides will play again, this time at Friend's Meadow, on Tuesday evening.
Halstead Town's tie at home to Tower Hamlets saw both teams agree to a penalty shootout to settle things, with the hosting Humbugs exiting the competition 7-5 on kicks.
It followed a 1-1 draw after the regulation 90 minutes - James Regan having put Halstead ahead - before Jordan Pavett dramatically equalised after Hamlets had gone ahead in the second half of extra-time.
Elsewhere, Newmarket Town suffered agony in extra-time at Enfield Borough, conceding twice to lose 4-2.
The Jockeys had gone behind before Stephen Spriggs sent them into the break one apiece before Charlie Bowen's header had put them into the lead.
But with just a couple of minutes to go, goalkeeper Alex Archer conceded a penalty from which Borough scored, before going on to get two more in extra-time.
Thurlow Nunn League First Division outfit Framlingham Town did make it through to the second round though, winning 2-0 at Cockfosters via a brace from Danny Smith.
In the Thurlow Nunn League Premier Division, Stowmarket Town racked up their third straight win and five in their last six games with a 4-2 home victory over Ely City.
Rick Andrew's ninth place side are now unbeaten in seven matches after Josh Mayhew, higher-league Bury Town's top goalscorer last season, took his tally this term to 22 in 18 games with all four against The Robins.
Hadleigh United, who hope to appoint a new manager by the end of next week, lost 2-1 at Fakenham Town, while Haverhill Rovers went down to the same scoreline at home to Kirley & Pakefield.
Mid-table Walsham-le-Willows recorded their first victory in eight attempts with a 2-0 home success over Mark Benterman's new-look Ipswich Wanderers side, with Jack Brame heading in one of the goals and Callum Dongray carrying off the man-of-the-match award.
Long Melford moved out of the bottom three with an excellent 4-1 victory at second-from-bottom Wivenhoe Town, with Steve Adams (2), Scott Sloots and TJ Le Page getting the goals.
It was a miserable day for Haverhill Borough though as they were thrashed 7-2 at Wroxham, with Ashley Botten and Ryan Swallow scoring.
In the Thurlow Nunn League First Division, Cornard United's Ryan Lines and Liam Aves got their first league victory on the board at the third attempt in some style, winning 5-1 at Needham Market Reserves to double their points tally and move off the foot of the table at their opponents' expense.
Stowmarket's Josh Mayhew was not the only one to score four on the day, with Lewis Blanchett the double, double and Myles Passley getting the other for the Ards, who made it back-to-back wins in all competitions, following their 2-0 First Division Knockout Cup win at Framlingham on Tuesday.
Elsewhere, Diss Town picked up all three points with a 2-1 win at home to Little Oakley, while AFC Sudbury Reserves had to settle for one after a 1-1 draw at home to Downham Town.
* For reaction to the weekend's games and the best local previews, see next week's print editions out on Thursday and Friday.