Boro started the game well, creating a few chances which mainly fell to Jake Reeves, and 20 minutes in Reeves took one of his sightings on goal and placed a fine strike from the edge of the box into the bottom corner of the Richmond net to open the scoring.
This seemed to spur Richmond into action and right on half-time they equalised with a fine strike from distance, ensuring scores were level at the break.
The second half started with Scarborough shooting into the wind, and the hosts played much better.
Reuben Staveley then scored with a shot from distance.
Aaron Holdsworth got the third goal for Boro, the Richmond keeper dropping the ball at the winger’s feet to tap home.
Aidan Crawford then grabbed the fourth for Alec Coulson’s side, firing home from close-range.
The goal of the game was saved for last when Holdsworth swung a lovely corner in for Louis Kille to rise above his marker and power a header into the top corner, the game finishing 5-1 to Athletic.
There were solid performances from Jack Scarborough, Ted Edwards, Liam Coulson, Max Wright and Josh Pickin.
Scarborough Athletic Under-12s were given a scare at Longhill Ravens as they fought back from 2-0 down to win 3-2 and maintain their 100% start to the campaign.
The hosts deserved their 2-0 lead at half-time as Boro shipped their first league goals of the season.
In the second half Boro found their rhythm and managed to get a grip on the game.
Charlie Eccles’ strike was half stopped on the line before Kobi Wilson followed in to make certain and Boro’s belief grew further as they halved the deficit.
Wilson then had a fine effort saved by the keeper before Lucas Hastie got Boro back on level terms with a right-footed volley from close-range.
With the game finely poised at 2-2, there was only one team likely to get a winner and Boro did just that when Harley Thornton’s strike from outside the box ensured all three points went back with the visitors.
Scarborough Athletic Under-16s welcomed Easingwold for a tense North Riding Cup tie and won on penalties.
Boro started well, playing to a good high tempo with Finlay Marsh and Dan Simpson creating a lot of opportunities in the final third, while at the back Harry Coldbeck was having another solid game.
Goalless at the break, it was the visitors who opened the scoring early in the second half with a smart low finish.
The lead lasted two minutes as Dan Simpson won possession and fed Kane Randerson-Wray, whose pinpoint cross found an unmarked Jaydan Hindle to head in the equaliser.
Two minutes later Boro were in front when a Zam Deans free-kick found its way to George Walmsley, who bundled the ball past the keeper.
Easingwold weren’t done yet though and they fashioned a well-worked equaliser that flew in off the foot of the post
Despite end-to-end action, neither team could find the winner and the game went straight to penalties.
Boro’s first four penalty takers, Marsh, George Walmsley, Lewis McGrath and Jaydan Hindle all scored, Cameron Anderson in goal for Boro dived brilliantly to his right to save Easingwold’s fourth, leaving Dan Simpson to coolly slot home the winning penalty.
A cracking cup tie which was a credit to both sides with Boro winning 5-3 on penalties.