After the euphoria of a late winner in the opening league game of the season at the weekend Chi suffered the heartache of defeat in the 89th minute as Oaklands Park hosted Step 4 football for the first time under the lights midweek.
Things couldn’t have begun any better for the home side who went ahead early on when Ricardo Thompson diverted a Rob Hutchings’ cross past his own keeper.
Whyteleafe, one of the league’s best teams on the road last season, almost replied immediately. Emmanuel Mensah, who shone all night, linked up with Antonio Walker-Barth but City captain Connor Cody managed to block the No10’s effort before fellow defender Corey Heath did the same with Renedi Masampu’s strike moments later.
In an intense first five minutes Lloyd Rowlatt forced Tyler McCarthy in the visitors’ goal into a smart save and then man of the match Scott Jones tested McCarthy with a shot on the turn.
The Chi back four had a number of set pieces to deal with in the early exchanges and this would prove to be an issue as the game progressed.
Matt Axell, who bagged both goals at Ramsgate, stung McCarthy's gloves before Ronald Sobowale equalised with a thunderous free-kick in the 22nd minute.
Jones and Gicu Iordache combined effectively in Chi’s next attack but the Romanian’s cross was just too long for Callum Overton. Next an Axell delivery found Heath at the back post but he headed just off target.
It was end to end stuff and Hutchings did well to turn Martin Sontan’s cross out for a corner before keeper Steve Mowthorpe was quick off his line to clear danger.
The hosts regained the lead five minutes before half time as Jones got a glancing header on a ball whipped in by Cody and might have gone into the break 3-1 up when a good chance fell to Overton.
Jamie Horncastle hobbled off after the restart having rolled an ankle. Kaleem Haitham came on and was involved in the action straight away linking up with Iordache who pulled a super parry out of McCarthy.
Whyteleafe were level once more in the 56th minute when Sobowale stabbed the ball in from close range following a Jordan Clarke free kick.
And he should have grabbed his hat-trick on the hour mark from the penalty spot but Mowthorpe made a fine save diving down to his right.
The home side had a storm to weather. Clarke found himself on the ball a lot as Chi conceded a catalogue of free kicks; a turn of blistering pace presented Walker-Barth with an opportunity; and Matt O’Donoghue went close in a spell that the Leafe dominated.
Iordache then almost caught McCarthy out with a clever set piece that pinged off the post before Jones headed a delivery from Rowlatt inches wide.
Clarke was instrumental in the winner when it came with a minute to go, snaking past three City players in the box before putting in a low cross that nicked in off Ben Pashley.
In time added on Overton almost grabbed Chi a precious and deserved point with a fierce shot McCarthy somehow got behind. After the match assistant manager Graeme Gee said, “It was a learning curve for our boys tonight. Every one of them gave their all.”
Chi are away at Bridon Ropes FC on Saturday in the preliminary round of the FA Cup (3pm) and return to Isthmian League action on Bank Holiday Monday at Burgess Hill (3pm).
Chichester - Mowthorpe, Heath, Hutchings, Axell, Cody, Pashley, Iordache, Horncastle, Jones, Rowlatt, Overton. Subs: Biggs, Clack, Davidson, Haitham, Bennetts.