Ross Embleton named a strong squad, captained by full-back Joe Widdowson. Conor Wilkinson returned to the Starting XI alongside Sam Sargeant, Jordan Maguire-Drew, George Marsh and Hector Kyprianou.
The early stages saw both teams probing each other as they found their feet, Jonson Clarke-Harris went close when he hit an effort on the half-volley from the edge of the box. His effort dipped over.
Conor Wilkinson found himself the first name in the official’s book on 15 minutes when he raced onto a loose pass and was brought down in the box, David Rock deciding it was a case of simulation.
The hosts took the lead just a minute later when a free-kick from the right touchline was whipped into the box, crashing off defender Alfie Kilgour and past Sargeant.
Leyton Orient responded well and equalised on 20 minutes when Maguire-Drew worked his way into the box and curled it towards the back post where Lee Angol was sniffing to tuck home.
Jordan Maguire-Drew was causing numerous problems, his cross from the right following a quick break-away was headed by Tony Craig against Kilgour, his own teammate, bouncing inches wide. Six minutes later, the winger struck from distance but Van Stappershoef was equal to it.
His impact on the game continued into the second half as the winger brought down Josh Wright’s cross-field pass, cut inside and let fly towards the far post but Van Stappershoef tipped away superbly.
However, just after the hour mark, the hosts grew into the game and had a series of good opportunities. The first came on 63 minutes when Clarke-Harris’ strike was palmed by Sargeant into the path of Tomlinson but he fluffed his lines on the rebound. Tomlinson was involved in the second chance as he got on the end of a good cross but directed his header wide.
Ollie Clarke almost won the game in the 87th minute when he drove an effort from the edge of the box, flying inches wide.
The game was decided on penalties, Bristol Rovers scoring all of theirs as Josh Wright and Ruel Sotiriou saw their efforts saved, sending the League One side through to the next round of the competition.
BRISTOL ROVERS: Van Stappershoef, Holmes-Dennis (Kelly 76), Craig, Upson (Tomlinson 58), Sercombe, Clarke ©, Clarke-Harris, Kilgour, Smith (Adeboyejo 46), Menayese, Rodman
SUBS: Jaakkola, Little, Nichols, Hargreaves
BOOKED: Holmes-Dennis (43)
GOALS: Kilgour (15)
PENALTIES: Clarke-Harris (scored), Rodman (scored), Craig (scored), Sercombe (scored).
LEYTON ORIENT: Sargeant, Ling, Widdowson ©, Ekpiteta, Wilkinson (Sotiriou 60), Maguire-Drew (Dayton 82), Angol (Harrold 73) , Marsh, Turley, Kyprianou, Wright
SUBS: Brill, Gorman, Happe, Dennis,
BOOKED: Wilkinson (14), Harrold (84)
GOALS: Angol (20)
PENALTIES: Wright (saved), Harrold (scored), Marsh (scored), Sotiriou (saved)
ATTENDANCE: 865 (106)