The Lions almost took the lead in the opening seconds with Gyimah Asante finding himself one on one with the goalkeeper before shooting tamely straight at him.
Hollington were undoubtedly in the ascendancy with the hosts happy to sit back and soak up the pressure which to their credit they did with great discipline and enthusiasm.
Luke Caister in the Hollington goal was largely a spectator however even he would have fancied his chances of notching the free header that stand in skipper Pat Willis ballooned over the bar from four yards.
The 0-0 scoreline at half time brought about a change in formation and this eventually paid dividends firstly with Pat Willis redeeming himself planting a powerful header into the top corner from a Patrick Kairaa corner and then Jamie Crone clinically finishing off an exquisite Harry Murphy through ball.
Crone forced another fine save from the Cuckfield goalkeeper as they clung on to any semblance of hope.
Seemingly out of nowhere Hollington switched off and Cuckfield pulled one back with their own set piece header and as the clock wound down Cuckfield equalised with an overhit free kick not too dissimilar to Ronaldinho’s in the 2002 World Cup with Caister enduring his own Seamen-esque moment.
Hollington dictated the game in extra time with Crone notching a not undeserved winner glancing a header from another corner into a despairing defender on the line who was unable to keep it out.
The same player almost secured his hat-trick with a spectacular bicycle kick only for the keeper to somehow tip it over the bar. There was one last scare for Hollington when Cuckfield rattled the crossbar from a ferocious 20 yard effort with virtually the last kick of the game.
Man of the match was American debutant Matty Bennani who produced a virtuoso midfield display.
Manager Asher Grindle said: "To be honest it was a bit of light relief from league action and a chance to give players on the periphery of the squad some well deserved minutes.
"Sadly not everyone performed at the level I had hoped for/expected which led to an uncomfortable afternoon and it will be a very different squad next Saturday.
"The Cuckfield gaffer was a great character and his lads did him proud. Overall it’s a case of job done for us and I’m pleased that we will have another opportunity to further extend our season."