A tall, quick, attacking midfielder, Ollie is at his best driving forwards from midfield with the ball at his feet. Capable of playing through the middle or out wide, he possesses excellent technique and a fine shot, as well as a competitive streak that he no doubt learnt from his older brother Max!

He made his debut for the club on the opening day of the 2014/15 season, playing an hour for the 2s in their 3-2 home win over KCS Wimbledon 2s - coincidentally the same game that Geoff Taunton-Collins made his debut in.

Ollie was a consistent presence in the 2s in his debut season and ended the campaign with 14 appearances under his belt and four goals, the first of which came in a 5-0 mauling of Malvern 2s in November - a game notable for the Harrow lineup that included three sets of brothers: the Orr-Ewings and the von Hirschs, as well as Ollie and his brother Max.

The following season Ollie appeared seven times for the 2s without finding the net, but he made up for that when making his 1s debut on the Harrow School astroturf in early March, scoring a superb hat-trick in the 10-1 demolition that included a candidate for Goal of the Season: the winger ran onto a raking 50-yard crossfield ball from David Lederman and struck a first-time volley that flashed across the box and into the far corner of the net. He played twice more for the 1s towards the end of the season, again scoring on the astroturf in the disappointing 4-3 defeat to Radley.

Ollie posted similar numbers in the 2s' 2016/17 promotion campaign, playing 8 games and scoring once - but again it was an absolute screamer, smashing the ball in off the underside of the bar from 25 yards out in the 3-2 win away to Salops 2s in early November. He also turned out twice for the 3s during the season.

2017/18 saw Ollie briefly lose his mind and volunteer to sail in the round the world yacht race that meant he missed the first half of the season. With brother Max joining him on the other side of the world for a work placement in Australia, the absence of the pair caused significant problems for skipper Geoff Taunton-Collins as he navigated a safe path through the choppy waters of Division Two.