Masterson's agent, Randy Rowley, has indicated that the pitcher is open to a long-term deal.
Along with Masterson, left fielder Michael Brantley, lefties Marc Rzepczynski and Josh Outman, and right-handers Vinnie Pestano and Josh Tomlin each turned in the proper paperwork prior to Tuesday's deadline.
Hours later, the Indians announced they had agreed to terms with Outman on a one-year deal.
Teams will exchange salary proposals with any unsigned arbitration candidates on Friday. If necessary, the arbitration hearings will take place from Feb. 1-21, but Cleveland has not gone to a hearing with a player since 1991.
Indians general manager Chris Antonetti will look to keep that streak alive this offseason with his group. Masterson's case carries the most weight, considering he projects to earn around $9 million-$10 million this year after settling on a $5,687,500 salary last season. Extension talks are expected to take place throughout the arbitration negotiations.
Last season, the 28-year-old Masterson won a career-high 14 games, turned in a 3.45 ERA, pitched three shutouts and ended the season with 195 strikeouts in 193 innings. He threw the first and last pitch of the regular season for Cleveland and earned a spot on the American League All-Star team in the middle of the summer.
Masterson has logged at least 180 innings in each of the past four seasons and was poised for a third straight season with at least 200 innings until an oblique injury sidelined him in September. Late in the month, while Cleveland pushed toward the AL's top Wild Card spot, the sinkerballer accepted a late-inning relief role, which he served in during the final week and in the AL Wild Card Game.
Cleveland's most prominent first-time arbitration case is Brantley, who hit .284 with 10 home runs, 26 doubles and 73 RBIs in 151 games last season. Over the past two years, the left fielder has hit a combined .286 with a .739 OPS and an average of 150 games per season. Brantley hit .375 with runners in scoring position in 2013 and ended the year with 11 outfield assists.
According to mlbtraderumors.com, Brantley could earn around $3.7 million through arbitration this offseason.
Rzepczynski (acquired from the Cardinals via trade in July) and Outman (reeled in from the Rockies in a trade this winter) each project to earn around $1.4 million through arbitration. Rzepczynski had 3.23 ERA (0.89 ERA with Indians) and held lefties to a .480 OPS in 38 games last season. Outman had a 4.33 ERA and limited lefties to a .539 OPS last year for Colorado.
Pestano and Tomlin are both entering their first winter of arbitration eligibility.
Pestano projects to earn around $1.3 million after posting a 4.08 ERA with 37 strikeouts in 37 appearances (35 1/3 innings) last season. The right-hander had a 2.45 ERA with 160 strikeouts across 137 games (132 innings) for the Tribe in the 2011-12 seasons, setting the club's single-season holds record (36) in '12.
Tomlin (projected to earn roughly $1.1 million) appeared in only one game for the Indians in 2013, but spent the bulk of the year rehabbing from Tommy John surgery on his right elbow. The starter has gone 23-19 with a 4.92 ERA in 60 career games for Cleveland in parts of four seasons. Tomlin, who will compete for a rotation or bullpen job this spring, has his best season in 2011, when he went 12-7 with a 4.25 ERA.