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Milan travelled to relegation-haunted Crotone looking to make up for a shock 2-1 San Siro defeat to struggling Empoli last week.
But for the second game in succession since the Rossoneri Sport Investment Lux bought the seven-time European champions from long-time owner Silvio Berlusconi, Vincenzo Montella's side disappointed.
Marcello Trotta fired Crotone into an eighth-minute lead at their Ezio Scida stadium and it took until the 50th minute for Milan to level, veteran defender Gabriel Paletta bundling home a messy goal from close range.
Milan pushed for a late winner but the Serie A giants, who saw Juraj Kucka sent off six minutes into second-half stoppage time for a second bookable offence, were forced to settle for a point.
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"We should be disappointed and angry for the result," Milan coach Montella told Mediaset Premium.
"We've found out to our cost that we can also drop points to teams much lower down in the table. We're going home with a point, and somewhat angry."
Milan remain sixth, five points adrift of Atalanta in the final Europa League spot, but for Montella -- given backing by the club's new owners last week -- a Europa League spot remains reachable, especially as the sixth-placed league finisher could be handed the spot allocated to the Cup winners.
In the June 2 Cup final, Juventus, set for a Champions League spot, face Lazio -- who look set to finish fourth and book a spot in Europe's second tier club competition.
"We still believe we can reach the Europa League," added Montella. "We've still to face Atalanta and sixth place still offers a way in."
Inter, enduring an equally tough season under new Chinese owners Suning, host Napoli in Sunday's late game looking for their first win in six outings.
A home win at the San Siro would pull Stefano Pioli's men level on points with Milan (59).
Roma's 3-1 derby defeat to Lazio earlier Sunday left them in second place at nine points behind runaway leaders Juve, but only four points ahead of Napoli, as they chase the second automatic Champions League qualifying place.
Keita Balde struck twice, either side of a Dusan Basta strike and Daniele De Rossi's goal for Roma, as Lazio ruined Francesco Totti's final derby to give Napoli a pre-game boost and ignite Lazio's hopes of fighting for a possible third-place finish.
After a disappointing Roma performance, coach Luciano Spalletti had to "keep quiet and accept the flak".
"We made some wrong decisions. We should have had more ball possession, but we struggled to respond when they went on the counter," he said.
Elsewhere, former Roma striker Mattia Destro struck in either half to complete a brace as Bologna secured their top flight survival with a comprehensive 4-0 win over Udinese.
It gave Roberto Donadoni's men a 13-point lead over third-from-bottom Crotone with four gammes remaining and Bologna forward Simone Verdi said: "We've deserved to stay up this season, so it's only right we celebrate."
Genoa and Empoli, however, face a nervous end to the season after defeats to Chievo and Sassuolo respectively left them just above the drop zone with four games remaining.
While rock-bottom Pescara's relegation last week was hammered home on Sunday by a 1-0 defeat away to Cagliari, fellow strugglers Crotone and Palermo can dream of top-flight survival for another week.
A point from their draw with Milan left Crotone third from bottom but now just four points behind Empoli.
But Crotone coach Davide Nicola remains unconvinced, saying: "We're neither closer, nor further away (from safety."
Palermo saw goals from Alessandro Diamanti and Haitam Aleesami, at the death, secure a 2-0 home win over 10-man Fiorentina -- only their fourth of the season. It left the Sicilians second from bottom and 10 points behind Empoli with four games remaining.