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| JANUARY, 2000 | |
| Date | Transaction |
| Jan. 19: | Oilers place defenceman FRANK MUSIL on the injured reserve for the rest of the season. Musil suffered a compressed vertebrae in his neck after a fall into the boards during practice Oct. 2. It is speculated that Musil's career may be over. |
| DECEMBER, 1999 | |
| Date | Transaction |
| Dec. 29: | Oilers acquire goaltender KAY WHITMORE from the Boston Bruins for defenseman MIKE MATTEUCCI. Whitmore, who has been assigned to the Long Beach Ice Dogs of the IHL, last played in the NHL during the 1994-95 season with the Vancouver Canucks. He has played 14 games for the Providence Bruins this season, posting a 6-6-1 record with a 2.86 goals-against average and a .907 save percentage. |
| Dec. 21: | Oilers name ANDERS HEDBERG director of European scouting. |
| Dec. 14: | Center DOUG WEIGHT is placed on the Injured Reserve List with cracked ribs. Weight was injured after being cross-checked by Gino Odjick of the New York Islanders. |
| Dec. 10: | Defenceman BRETT HAUER is reassigned to Manitoba of the International Hockey League. Hauer scored 0-2-2 in five games since his call-up. |
| Dec. 7: | The last of the Oilers' unrestricted free agents is signed, as MARTY MCSORLEY inks a one-year deal with the Boston Bruins. McSorley played 46 games with the Oilers last season, scoring 2-3-5 and collecting 101 PIMs. He was not in the team's plans this year. |
| Dec. 2: | Oilers sign unrestricted free agent left-winger MICHEL PICARD to an undisclosed contract. The 30-year-old Picard has played 157 games in the NHL with Hartford, San Jose, Ottawa and St. Louis, scoring 27-38-65. |
| Dec. 1: | In a swap of minor league centers, the Oilers obtain center ROB MURRAY from the Phoenix Coyotes for center ERIC HOUDE. Murray has been asssigned to the Hamilton Bulldogs of the American Hockey League. |
| Dec. 1: | Oilers reassign left winger PAUL COMRIE to Hamilton. |
| NOVEMBER, 1999 | |
| Date | Transaction |
| Nov. 29: | Goaltender ERIC HEFFLER is reassigned to Hamilton. |
| Nov. 29: | Oilers recall defenceman BRETT HAUER from the Manitoba Moose of the IHL. Hauer, the IHL's leading scorer with six goals and 22 assists this year, last played in the NHL in the 1995-96 season, when he dressed for 29 games with the Oilers. |
| Nov. 25: | Two more Oilers are placed in the injured reserve list. Right winger MIKE GRIER (fractured right clavicle) and left winger ETHAN MOREAU (torn rib cartilage) will both be out of the lineup indefinitely. |
| Nov. 25: | Oilers place goaltender BILL RANFORD on the injured reserve list with an inner ear infection and recall goaltender ERIC HEFFLER from Hamilton. |
| Nov. 4: | Oilers place right winger REM MURRAY on the injured reserve list. Murray is expected to be out of the lineup for 10 to 12 weeks with a torn medial collateral ligament in his right knee. Center PAUL COMRIE, who had been earmarked for Hamilton after Bill Guerin re-signed, will stay in Edmonton and fill Murray's roster spot. |
| Nov. 2: | Oilers re-sign free agent right winger BILL GUERIN to a two-year contract worth a reported $5.7 million U.S. The deal calls for $2.6 million in base salary this season and $3.1 million for the 2000-2001 season, plus incentives. |
| OCTOBER, 1999 | |
| Date | Transaction |
| Oct. 29: | Oilers re-assign left winger DANIEL CLEARY to Hamilton. |
| Oct. 18: | Oilers recall defenseman/left winger BERT ROBERTSSON from Hamilton and reassign defenseman BRAD NORTON to the Bulldogs. |
| Oct. 14: | Oilers recall left winger DANIEL CLEARY from Hamilton. |
| Oct. 7: | Left-winger ESA TIKKANEN signs an undisclosed contract with Hamilton. |
| Oct. 6: | Oilers re-assign left-winger DAN LACOUTURE to Hamilton. |
| Oct. 5: | Oilers re-sign right winger MIKE GRIER to a one-year, $675,000 contract. |
| Oct. 4: | Oilers recall defenceman BRAD NORTON from Hamilton to fill in for defenceman FRANK MUSIL, who was injured in practice. Musil moves to the injured reserve list. |
| Oct. 1: | Oilers trim their roster to 23 players, re-assigning center ERIC HOUDE and defenceman BRAD NORTON to Hamilton. |
| Oct. 1: | Oilers sign center PAUL COMRIE to a two-year contract and left winger RYAN SMYTH to a one-year deal. Comrie's deal is reported to pay him a $200,000 signing bonus plus $475,000 in the first year and $525,000 in the second. Smyth's contract is for $675,000. |
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