Barry Town United and Cardiff Met face Uefa Europa League tests against teams from Northern Ireland and Luxembourg.
The preliminary round draw was made in Nyon, Switzerland with 14 teams involved.
Manager Gavin Chesterfield and his Barry players will face Cliftonville, while Christian Edwards’ Met students take on Luxembourg outfit Progrès Niederkorn.
Barry will be home in the first leg at Leckwith Stadium, Cardiff on Thursday, June 27 with the away leg played a week later on Tuesday, July 4.
The Met are away in the first leg against Niederkorn and will also play their home leg at Leckwith Stadium.
Cliftonville, are Ireland’s oldest football club, formed in 1879, and they finished fifth in their league before beating Coleraine and Glentoran in the Europa League play-offs.
Met opponents Progrés have won the Luxembourg National Division three times, although their last trophy was earned in 1981. They finished fourth in 2018-19.
Connah’s Quay Nomads were not involved in the preliminary round draw and enter the competition in the next round.
The students earned a penalty shootout win against Bala Town in the Welsh Premier League play-off final.
Met will receive £193,000 prize money for qualifying, but their players won’t be rewarded with a bonus despite taking their place in Europe for the first time in the club’s history.
Instead they pay £150 membership fees and most put in a lot of effort on about course work and assignments.
It’s the same for Cardiff Met Women, who are in the Champions League qualifiers.
“A lot of people can’t comprehend players paying to play,” said manager Edwards, a former Swansea City, Nottingham Forest and Bristol Rovers defender from Caerphilly.
“Nobody is pushed into signing for us – they sign because they know the implicit rules.
“They see an added value of that dual career athlete where they can have an education and still play sport at a high level and that fits in with what they do.
“We develop them as young men to have good career prospects and that they play football at as high a standard that they want.
“We won’t be able to pay the players, but what we offer them then is an opportunity to play European football and that will be our unique selling point.”
The Archers finished seventh spot in the Welsh Premier League secured a place in the end of season play-off and they won 3-2 at Caernarfon Town in the semi-finals to secure their place in the final.
The climax to the Welsh Premier League season coincided
Cardiff Met are the first British university men’s side to play in European competition, while the women’s team have also qualified for Europe.
Kerry Harris’ team won a trophy treble and did not lose a match over the season.
“Kerry and the girls beat everyone put before them and it’s testimony to the hard work they put in,” said Edwards.
“It’s brilliant for a university that has traditionally been a rugby university to have two football teams playing in Europe. That is not only unprecedented here in Wales, but the UK and probably Europe.
“It’s a great summer of football for the men’s and women’s teams and it just goes to showcase Cardiff Met as a football institution that’s firmly on the map.”
Preliminary round (ties to be played June 27/July 4)
Progrès (Luxembourg) v Cardiff MU (Wales)
La Fiorita (San Marino) v Engordany (Andorra)
Sant Julià (Andorra) v Europa (Gibraltar)
Ballymena (Northern Ireland) v NSÍ (Iceland)
Prishtina (Kosovo) v St Joseph’s (Gibraltar)
Tre Fiori (San Marino) v KÍ Klaksvík (Iceland)
Barry Town (Wales) v Cliftonville (Northern Ireland)