On Wednesday, the 45-year-old will find himself in a seat at the San Siro he never envisaged being privileged to, as he leads Sicilian side Trapani from the dugout into battle with the Serie A giants in the fourth round of the Coppa Italia.
Boscaglia, who failed to make the grade as a player, has guided Trapani to three promotions in four seasons to reach Serie B for the first time in the club's history.
A Coppa Italia scalp is the midweek target for a club experiencing dizzying levels of success, as they take on an Inter side that has kicked on from the disappointment of missing out on a top-eight league finish last term.
Trapani were 1-0 winners against promotion-hunting Virtus Lanciano on Saturday, and sit comfortably in mid-table as they settle down in the second tier.
Boscaglia is wary about expecting too much from the trip to Milan, and there was a time when he would have been firmly behind the home side.
"I started by supporting Juventus, as my dad did," Boscaglia told the Giornale di Sicilia. "But then I decided to follow my brother's passion, which was Inter."
Ahead of the trip north for the highest-profile match in the club's history, Boscaglia said: "It's a dream that I thought impossible.
"I've always said without false modesty when I started my career as a coach that I intended to get as high as possible, but I never thought that I'd be back at the San Siro to play against Inter.
"We are going to the San Siro hoping to make a good impression, but we know that we will face a team that three years ago won everything there was to win in the world."
It was a Jose Mourinho team, of course, that lifted the Serie A, Coppa Italia and Champions League titles in 2010, adding the Club World Cup after the Portuguese head coach's departure to Real Madrid.
Despite the latter title, Inter have not been the same team since Mourinho's departure.
They stand fourth in Serie A this time around, but coach Walter Mazzarri bristled at the weekend performance in drawing 1-1 with Sampdoria, saying the display was "the worst game my team has played this season", and he will be expecting a positive response.
With the top eight finishers in Serie A last season handed byes to the last 16, this week's eight ties will provide the opposition for those teams in the next round in January.
Tuesday sees Bologna face Siena, Spezia encounter Pescara, Avellino take on Frosinone and Parma tackle Varese. Frosinone are the lowest-ranked team left in the competition, hailing from Lega Pro1B.
Along with Inter's match on Wednesday, Chievo play Reggina and Atalanta will have home advantage against Sassuolo. Thursday sees Verona travel to face Sampdoria.