With the purchase of IPX Air and its airline operating certificate in 1987, UPS acquired its first 25 pilots. Within a few short years, the Company grew from a handful of pilots to nearly a thousand by the end of the decade. With no representation, UPS introduced the pilots to the International Brotherhood of Teamsters and Local 608 was formed to represent both the pilots and mechanics. Contract talks began in the fall of 1987 and ended in December. An agreement was finalized in January of 1988.

With a labor agreement in place, the UPS Air Division exploded. More than 800 pilots were hired in 1988 alone. However, the substandard nature of the pilot group's first contract was becoming evident. Poor schedules, working conditions and pay were taking a toll on the growing pilot group.

It was during this time, a handful of UPS pilots began discussing the possibility of switching union representation. Two of the most vocal crewmembers were terminated after expressing their desire to be represented by the Airline Pilots Association. Several pilots who had served as union stewards for the Teamsters realized it would take a new, independent union to bring about change.

On October 27, 1989, the pilots began circulating National Mediation Board "authorization to act" cards on UPS property. In the following days, 700 pilots would sign the cards calling for a National Mediation Board election.

Under armed guard, the ballot count held at the NMB's Washington, D.C. headquarters was decisive. 757 ballots were cast for the IPA, 7 for the IBT and 2 write-ins for ALPA. On January 10, 1990, UPS received official notification that the Independent Pilots Association would be the collective bargaining unit for UPS pilots. By August, the Association was ready to begin negotiations with the Company.

Under the direction of the NMB, talks between UPS and the IPA intensified. In October 1991, the parties met for three weeks virtually around the clock. A tentative agreement was announced on October 27, 1991-- fifteen months after negotiations began and two years to the day from when the IPA authorization cards had been circulated.

Much was gained in the new contract: improved pay with full retroactivity with a trip and duty rig system; a stronger scope clause; no B scale; scheduling improvements and enhancements in the area of vacations. However, the contract was just a foundation upon which to build.

Negotiators for UPS and the IPA returned to the bargaining table in 1996. In August of 1997, 100% of the IPA membership honored the Teamsters picket lines during their two-week strike. A tentative agreement between the IPA and UPS would come in January of 1998. This second contract introduced a basic Defined Benefit pension plan with retroactive service credit to the airline's founding in 1988.

The IPA and UPS entered negotiations for their third contract in October, 2002. These talks utilized the principles of the National Mediation Board's Interest Based Bargaining; a process that stresses joint problem solving and mutual gain. The IPA/UPS talks, which began prior to the pilot contract's December 31, 2003 amendable date, are the first pilot talks to be facilitated under IBB throughout the entire direct negotiation phase.

Negotiations were put on hold from October 21, 2003 to January 2004 due to the IPA Presidential election. In December 2003, 747 Captain Tom Nicholson was elected IPA President, succeeding founding IPA President 757 Captain Robert Miller.

Contract negotiations between the IPA and UPS resumed January 19, 2004. In March, the IPA and UPS mutually agreed to extend Interest Based Bargaining through July 1, 2004. It wasn't until June 30, 2006 that IPA and UPS negotiators reached a tentative agreement. On Aug. 31, 2006, the IPA membership ratified the new contract. This third contract resulted in increased compensation, retirement and benefits along with comprehensive work rule improvements and additional scope clause protections.

In December 2006, the membership elected Robert Miller (founding President) and Secretary, Rick Derthick. Miller succeeded Tom Nicholson and Derthick succeeded founding Secretary Herb Hurst.