The Redwing Varsity team finished 3rd in the CCHL play with a 15-7-2 record. During the Kennedy Cup playoffs, Varsity defeated St. Rita in the quarter finals, then lost to Providence in the last 25 seconds of game three in the semifinals. In the Blackhawk Cup State playoffs, the Redwings beat St. Viator to advance to the round of 16 but fell to Glenbrook North in the quarter finals. The Junior Varsity team finished 5th in the CCHL play with a 8-8-0 record. JV qualified for the DiCristina Cup playoffs, sweeping Marmion in the first round (2-0) before falling to the eventual champion, Fenwick, in OT of game two in the semifinals.

The Redwings Varsity team finished 2nd in the CCHL league play with a 17-3-0 record and the Junior Varsity finished 6th with a 11-7-2 record. Both teams qualified for league playoffs. JV lost in the first round of the DiCristina Cup playoffs to Fenwick. Varsity defeated Marmion in the quarter finals, and beat Fenwick in the semi-finals to advance to the Kennedy Cup Finals but lost to St. Ignatius in a competitive series. In the Blackhawk Cup State playoffs, #9 Varsity Redwings beat #8 Glenbrook North in Double OT to advance to the Elite 8, falling to #1 New Trier Green in quarter finals. Redwing Hockey Club Director and Varsity Head Coach Jon Grzbek was inducted into the Illinois Hockey Hall of Fame as the member of the 17th class of inductees.

For the first time in three seasons, the Redwings rostered only two teams. The reduction of teams, however, did not affect the success of the club as a whole. The JV team placed second in the CCHL with a 13-3-0 record which qualified them for the DiCristina Cup post season tournament where they fell in the semi-finals in a hard-fought loss to Providence. Varsity finished second in the CCHL with a 17-1-2 record. A Kennedy Cup run saw Varsity defeat Fenwick in the quarter finals and Providence in the semi-finals to advance to the Kennedy Cup Finals against St. Ignatius. In a dramatic three game series, the 2020-2021 Redwings became the first team in club history to repeat as Kennedy Cup Champions by besting St. Ignatius in game 3, 6-5 in OT. The 2021 State Championship was cancelled due to COVID-19 but the collective high school hockey clubs put together their own tournament. Varsity failed to advance past the preliminary round and JV fell in the semi-finals to GBN.

For the second consecutive year, the Redwings fielded three teams. In CCHL regular season play, Varsity Red finished 17-2-1-0 (2nd) and completed a storied playoff run, capturing the coveted Kennedy Cup title, the club’s third, in a hard fought three-game series vs Providence in OT! JV finished 9-9-2-0 (6th) losing to Marist in the first round. Both made Sweet 16 in the State Championships. In their second year of IHSHL league play, Varsity White competed hard against tough competition and improved all season with a strong showing in their Thanksgiving tournament and playoff bracket.

The Redwings fielded three teams for the first time in club history, adding a second Varsity team (White) playing in the IHSHL West. Varsity Red kicked off the season going back-to-back once again in the Belle Tire Back to School Classic. Varsity White had early success in their inaugrual season with a runner up finish in the MyHockey Pre-season challenge. In CCHL regular season play, Varsity Red finished 5th and went on to a top 8 seed in state, JV finished 4th. Both teams made the quarter finals of the CCHL playoffs. Varsity Red made the Sweet 16 in the State Championships once again. Varsity White had a strong showing through the tiering round of playoffs in their team debut.

The Redwings had a great season  They finished the year without playing a full game with all players healthy but the never give up spirit endured.  After taking a year off, they once again captured the championship at the Belle Tire Back to School Classic tournament in Detroit.  They advanced to the semi-finals in the Kennedy Cup race after defeating Providence in a tough first round match-up.  The Redwings advanced to the Sweet 16 in the Blackhawk Cup.  JV lost in the semi-finals of the CCHL playoffs and advanced to the Sweet 16 in the state championships.

Varsity finished strong in the CCHL earning the 2nd place spot, but fell to a physical Br. Rice team in Kennedy Cup play. For the 3rd consecutive year, the Redwings advanced to the Final Four in the State Tournament with a big win over GBN. They couldn’t get past a faster and stronger New Trier Green team to make it to the Blackhawk Cup finals. JV began the year with the largest Freshman class in club history. They finished in 4th place in the CCHL and for the 5th straight year made it to the Sweet 16 in the Blackhawk Cup before falling to St. Viator in the Elite 8. 

The varsity team had a very successful season.  They posted the best record in the state and Benet Hockey history. They repeated as champions of the Belle Tire Tournament and went undefeated in winning the O’Grady Cup in the prestigious Loyola Thanksgiving Tournament. They had the unique opportunity to play the United States Women’s National Team and were the only team to beat them in an exciting overtime thriller.  They advanced to the Final Four of the Blackhawk cup for the second straight year.  They advanced to the Kennedy Cup finals where they lost a hard fought series 2-1.  The JV team advanced to the round of 16 of the Blackhawks Cup. 

 Varsity finished 1st in regular season and went on to recapture the Kennedy Cup from Providence. In the Blackhawk Cup the team lost a heartbreaker in OT to GBN in the championship game at the UC.  JV lost in the finals of CCHL playoffs after finishing 1st in the regular season and advanced for the second year in a row to the Final 4 in state.
 

Varsity fought hard to keep the Kennedy Cup at Benet but lost in finals to Providence. The Varsity team once again fell to Providence in the Final 8 in State. The Junior Varsity team lost in the first round of the CCHL playoffs but made a strong showing in the state tournament losing to Fenwick in OT in the Final 4. They were the first Benet JV hockey team to advance this far in the State playoffs. 

Varsity rallied to bring home the coveted CCHL Kennedy Cup for the first time in Benet history, defeating Fenwick. They made it to the Final 8 in the Blackhawk Cup State Championship.  The Junior Varsity team made the CCHL playoffs but lost in first round. They lost in the final 16 round of the State playoffs. 
 

The Redwings set attendance records and made history with their first appearance in the Catholic League championship. Varsity finished second in the Catholic League and made it to the Final 8 in state. JV also finished strong, playing in the ISHL championship game.
 

With 11 wins in league play, Varsity’s first year in the Catholic League was a success. 

The club entered the Catholic League with the JV team included formally and Varsity playing 10 games against League teams. The club was led by a new Director of Hockey, Jon Grzbek. Andrew Schlie joined the club as Associate Coach. The season ended with winning records for both Varsity and JV.
 

For the first time, the club fielded both Varsity and Junior Varsity teams. Both teams had winning records: Varsity 14-12-2 and JV 18-5-4. The coaching staff included two former Redwing players as assistant coaches: Greg Brouman and Drew Tierney.