The New Saints and Fiorentina play their first match of the UEFA Conference League league phase on Thursday when they meet at the Stadio Artemio Franchi in Florence.
Fiorentina v The New Saints is available to watch live in the UK on TNT Sports 4.
Fiorentina v The New Saints will kick off at 20:00 BST on Thursday 3rd October and will be played at the Stadio Artemio Franchi in Florence, Italy.
The New Saints have played 79 matches in European competitions since their first appearance (as TNS Llansantffraid) in the 1996-97 UEFA Cup Winners' Cup, but this will be their first game against Italian opposition.
The Welsh side have arrived in the UEFA Conference League after participating in qualifying rounds for both the UEFA Champions League and the UEFA Europa League.
They beat Lithuanian side Panevezys 3-0 on aggregate in the Champions Path of the play-off round to reach this stage, but the Serie A side surprisingly had a tougher time reaching this stage.
Fiorentina were taken all the way to a penalty shootout by Hungarians Puskas Academika, drawing 3-3 at home and 1-1 after extra-time in the away leg.
The New Saints are fifth in the Welsh Premier this season after winning five of their first seven matches, but have three games in hand on the teams above them due to their European commitments.
La Viola are 11th in Serie A having taken seven points from their first six games.
La Viola have a host of unavailable players for the first leg, largely due to the dramatic finish to their tie against Puskas in the previous round.
Luca Ranieri, Pietro Comuzzo and Lucas Martinez Quarta are all suspended after receiving red cards in that game.
The Italian team's defence could be further depleted if Marin Pongracic is not passed fit, while midfielder Rolando Mandragora is also an injury doubt.
Midfielder Abdelhamid Sabiri and goalkeeper Oliver Christensen were not registered to play in this competition.
Jordan Williams is serving the final game of his suspension for a red card in the UEFA Europa League game against Petrocub.
Harrison McGahey, Matthew Olosunde and Ash Baker are unlikely to feature due to injuries and fitness concerns.