- Pisa finished 20th in Serie A in 2025-26, getting relegated with just 18 points.
- Empoli finished 15th in 2025-26 Serie B with 41 points - good for safety but no more.
- Empoli's 3-1 and 2-1 wins in 2020 and 2020 have given them the edge in their recent meetings.
A cagey cup clash in prospect
Pisa's recent form has been mixed, to say the least, closing 2025-26 with a run of five straight defeats before posting a 6-1 friendly win over Pavia and then a 1-1 draw with Juventus Next Gen. However, Empoli's form has been similarly erratic, with an 8-0 demolition of a Castelfiorentino United side in preseason giving way to a 1-1 away draw with Spezia.
Paolo Bianco has set up Pisa in a pragmatic style this season, with a compact back-three and a desire to control the ball in the midfield and counter-press when it is turned over. This style clash could be a chess game on Monday, with Pisa looking to overplay the wide areas and Empoli looking to shut up the middle and then break quickly in behind.
Mattéo Tramoni was probably Pisa's liveliest outlet last season, scoring a few goals and making the runs that can stretch the back three when the game is close. He scored in preseason and is capable of hurting the Azzurri with a late run or two.
Empoli's forward depth will be key, with Bogdan Popov and Flavio Bianchi likely to play at some stage of the game and they both provide a very different threat to the main goal man Stiven Shpendi. He is a poacher with some flair, but his movement is the key aspect to his game and he can punish Pisa if they over-commit.
Guido Pagliuca has set up his side to play a disciplined 3-5-2 or 3-4-2-1 system, built on a compact defence and fast vertical transitions. They have the edge in the recent head-to-head record, winning three of the last five, but Pisa's home ground advantage should see them through to penalties if not the next round.
Pisa’s price is a little tight
The bookmakers have made the hosts slight favourites for this clash, with Pisa 1.9 and Empoli 3.9, with the draw coming in at 3.45.
Pisa's 2025-26 Serie A campaign was brutal and their defence had big holes in it. However, any lapse in concentration or complacency could cost them against a decent Serie B side, so we're going to swerve the hosts and go with Empoli to snatch the win or at least make it to penalties after 90 minutes.
Under 2.5 goals at 1.7 looks like a match the bookies have set to suit the script of this game - tight, cagey and low-scoring, and with the both teams to score market sitting right on the knife edge, it's probably the best we can get from this one.
