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8 June 2020

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Toby Holland, Anthony Cheshire and Massimo Giamattei have already agreed deals to become professional footballers and a new chapter starts for all three of them once football returns.

However, the trio’s journey together started all at the same time. Back in 2016, they all joined the Swindon academy within weeks of each other.

Anthony Cheshire started a week earlier than his more forward-thinking team-mates who joined a week after pretty much on the same day.

They will begin life as professional footballers once Richie Wellen’s side return to first-team action with attacking midfielder Toby Holland coming off the back of an excellent season in the under-18s as well as breaking into the first-team picture in domestic cup competitions earlier in the campaign.

After getting to know, Anthony and Mass, spoke to Toby to hear about his journey so far.

Toby – congratulations on your first professional deal. Talk us through how you first start with the Swindon academy.

I was playing local Sunday and Saturday league football and I was actually on trial at Birmingham for six or seven weeks before I came to Swindon. While I was at Birmingham, I was also playing for my Sunday side.

We were playing a semi-final against Cirencester Town at around under-14 level and Swindon were scouting someone from the other team. They actually approached my coach after the game because I’d played quite well and scored a couple of goals and we’d won 2-1.

They just asked who I was playing for. I was on trial at Birmingham still but once that came to an end, I got in contact with Swindon.

It’s weird actually because me, Mass and Chesh all started and singed at the same time. When I came in, Chesh had been there for about a week or so and Mass and I came in at exactly the same time and we were all signed between three weeks. We’ve done it all together since then.

How did you find moving to an academy set-up?

I found the new environment really different – I’d never been involved with academies up until then really. I did a tiny bit with Cheltenham but nothing serious.

When you got to an academy, the training is just so much better – you’re doing drills rather than before it’s more of a kickabout. They’re teaching you things and certain ways of playing the game – you do so much fitness.

There’s a hell of a lot more coaching staff, it’s more structure and well drilled.

When you arrived what struck you about the way Swindon played throughout the age groups?

I always felt like Swindon wanted to play more with the ball – other academies in the League One and League Two academies had big lumps playing for them and they just wanted to win headers and fight more than really play.

I think Swindon really suited me as a player because they wanted to play that sort of football. That’s benefited me because that’s my preference too.

At 16, you moved up into the scholarship programme – how was that transition?

It was very different. You go straight into pre-season and we were training double sessions every day. I was getting on the bus back to my digs, which was a good 40 minutes away, and I was fighting to stay awake.

I used to drop to sleep on the bus, wake up and miss my stop. That happened to me quite a lot during that first pre-season. I remember it just being so hard at that point being awake and really alive, concentrating and doing all the running. For a lot of us, that was a big shock.

You were doing really well with Dave Farrell’s Under-18s side before the academy fixtures were cut short – what are your reflections on the 2019/20 season?

It was around November time where we found our feet and our best formation – we kicked on from there. I think it was an 11 or 12 unbeaten streak. I was doing well and scoring goals, for my position.

We were on a roll when it came to an end. It’s a shame that it got cut short but it was still a good season for me overall. I think I ended up top scorer actually, just to throw that one in there. It was a great season while it lasted.

During this year, you’ve been part of the Trophy squads and made your debut in that competition – how good was that experience?

It was amazing just to be in and around it. Even if we didn’t get on, getting that insight into what a proper matchday was like was so different. I thought it would be more serious than it was but there’s a good level of calm.

There was a lot of banter on the days we were with the first-team.

I get on with Keshi (Anderson) really well. He’s probably the person I speak to and have asked for advice the most. I got on with Tyler Reid because he was playing in the Trophy – Tom Broadbent helped me out too.

What has the coaching been like in the lead-up to signing your first pro deal?

Playing under Noel Hunt was pretty special because of what he’s done in his career but also because of the way he was with the young lads. He spoke to us and got us involved – made sure there was no awkwardness or people getting worried.

Playing for the club for four years, Alan McLoughlin has always been in and around it. He had just become Academy Manager when I joined – he’s helped me a lot since under-16s a lot. He’s quite hard on me but does it all for the right reasons. I appreciate that so much because I don’t think I would have pushed on otherwise.

Dave Farrell has been a good coach and great laugh in the last two years. He helped me out a lot.

What are you most looking forward to about making the step into professional football?

I’m looking forward to going into that sort of environment – it’ll be massively different to the under-18s. I think training will be a lot quicker, a better standard. That gives you the opportunity to showing what you can do and impressing.

In the academy everyone knows what you’re about but going into a new environment it gives you a new set of people to show what you can do. We’re sat around waiting at the moment and I can’t wait for it to end so we can get back.

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